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Revision as of 08:58, 20 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'StdInChI', 'StdInChIKey').← Previous edit		Latest revision as of 23:58, 2 December 2024 edit undoInnerstream (talk | contribs)Autopatrolled, Extended confirmed users4,150 edits →Natural production
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	| Verifiedfields = changed		| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 410170050		| verifiedrevid = 456486843
	| ImageFileL1 = Vanillin2.svg		| ImageFileL1 = Vanillin2.svg
	| ImageFileL1_Ref = {{chemboximage|correct|??}}		| ImageFileL1_Ref = {{chemboximage|correct|??}}
Line 9:		Line 9:
	| ImageFileR1_Ref = {{chemboximage|correct|??}}		| ImageFileR1_Ref = {{chemboximage|correct|??}}
	| ImageNameR1 = Spacefill model of a vanillin minor tautomer		| ImageNameR1 = Spacefill model of a vanillin minor tautomer
			| ImageFile2 = File:Hydrazin síran.jpg
	| PIN = 4-Hydroxy-3-methoxybenzaldehyde{{Citation needed|date = October 2011}}
			| PIN = 4-Hydroxy-3-methoxybenzaldehyde
	| OtherNames = Methyl vanillin{{Citation needed|date = October 2011}}<br />
			| OtherNames = Vanillin<ref name=Vanillin>{{cite web|url = http://sci-toys.com/ingredients/vanillin.html |title = Vanillin|first = Simon Quellen|last =Field|website = sci-toys.com}}</ref><br />Methyl vanillin<ref name=Vanillin/><br />Vanillic aldehyde<ref name=PubChem>{{PubChem|1183}}.</ref>
	Vanilin{{Citation needed|date = October 2011}}<br />
			|Section1={{Chembox Identifiers
	Vanillic aldehyde{{Citation needed|date = October 2011}}
			| IUPHAR_ligand = 6412
	| Section1 = {{Chembox Identifiers
	| CASNo = 121-33-5		| CASNo = 121-33-5
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| PubChem = 1183		| PubChem = 1183
			| ChemSpiderID = 13860434
	| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 13860434
			| UNII = CHI530446X
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = CHI530446X
			| EINECS = 204-465-2
	| UNII_Ref = {{fdacite|correct|FDA}}
	| EINECS = 204-465-2		| KEGG = D00091
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D00091
			| MeSHName = vanillin
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| MeSHName = vanillin		| ChEBI = 18346
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 18346
			| ChEMBL = 13883
	| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 13883
			| RTECS = YW5775000
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| RTECS = YW5775000		| Beilstein = 472792
	| Beilstein = 472792		| Gmelin = 3596
	| Gmelin = 3596		| 3DMet = B00167
			| SMILES = c1(C=O)cc(OC)c(O)cc1
	| 3DMet = B00167
			| StdInChI = 1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,8H,1H3
	| SMILES = COC1C=C(C=O)C=CC1=O
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
	| StdInChI = 1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
			| InChI = 1/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
	| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = MWOOGOJBHIARFG-UHFFFAOYSA-N
	| InChI = 1/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
	| StdInChIKey = MWOOGOJBHIARFG-UHFFFAOYSA-N
			| InChIKey = MWOOGOJBHIARFG-UHFFFAOYAS
	| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
	| InChIKey = MWOOGOJBHIARFG-UHFFFAOYAS
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 8		| C=8 | H=8 | O=3
			| Appearance = White solid
	| H = 8
			| Odor = Vanilla, sweet, balsamic, pleasant
	| O = 3
			| Density = 1.056 g/cm<sup>3</sup><ref name=crc1>{{cite book | editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 978-1-4987-5429-3|page=3.310}}</ref>
	| ExactMass = 152.047344122 g mol<sup>-1</sup>
			| MeltingPtC = 81
	| Appearance = White crystals
			| BoilingPtC = 285
	| Odor = Floral, pleasant
			| MeltingPt_ref=<ref name=crc1/>
	| Density = 1.056 g cm<sup>-3</sup>
			| BoilingPt_ref=<ref name=crc1/>
	| MeltingPtKL = 354
	| MeltingPtKH = 356		| Solubility = 10 g/L
	| BoilingPtC = 285		| LogP = 1.208
			| VaporPressure = >1 Pa
	| Solubility = 10 g dm<sup>-3</sup>
	| LogP = 1.208		| pKa = 7.781
	| VaporPressure = >1 Pa		| pKb = 6.216
	| pKa = 7.781
	| pKb = 6.216
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| CrystalStruct = Monoclinic		| CrystalStruct = Monoclinic
	}}		}}
	| Sectino4 = {{Chembox Thermochemistry		|Section4={{Chembox Thermochemistry
	| DeltaHc = -3.828--3.828 MJ mol<sup>-1</sup>		| DeltaHc = −3.828 MJ/mol
	}}		}}
	| Section5 = {{Chembox Hazards		|Section5={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| GHSPictograms = {{GHS exclamation mark}}		| GHSPictograms = {{GHS exclamation mark}}
	| GHSSignalWord = '''WARNING'''		| GHSSignalWord = '''WARNING'''
	| HPhrases = {{H-phrases|302|317|319}}		| HPhrases = {{H-phrases|302|317|319}}
	| PPhrases = {{P-phrases|280|305+351+338}}		| PPhrases = {{P-phrases|280|305+351+338}}
			| NFPA-F = 1
	| EUClass = {{Hazchem Xn}}
	| NFPA-F = 1		| NFPA-H = 1
	| NFPA-H = 1		| NFPA-R = 0
	| NFPA-R = 0		| FlashPtC = 147
	| FlashPt = 147 °C
	| RPhrases = {{R22}}
	}}		}}
	| Section6 = {{Chembox Related		|Section6={{Chembox Related
	| OtherCpds = ]<br />		| OtherCompounds = ]<br/>]<br/>]<br/>]<br/>]
	]<br />
	]
	}}		}}
	}}		}}
	'''Vanillin''' is a ], an ] with the molecular formula C<sub>8</sub>H<sub>8</sub>O<sub>3</sub>. Its ] include ], ], and ]. It is the primary component of the extract of the ] bean. It is also found in '']'',<ref name= floralibrary>{{cite web|url=http://www.floralibrary.com/flora/leptotes/bicolor		'''Vanillin''' is an ] with the molecular formula {{chem2|auto=1|C8H8O3}}. It is a ]. Its ] include ], ], and ]. It is the primary component of the extract of the ]. Synthetic vanillin is now used more often than natural vanilla extract as a ] in foods, beverages, and pharmaceuticals.
	|title= Leptotes bicolor|publisher=Flora Library|accessdate=2011-08-21}}</ref> roasted coffee<ref>{{cite doi|10.1002/ffj.2730100102}}</ref> and the ]. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a ] in foods, beverages, and pharmaceuticals.
	Vanillin as well as ] is used by the food industry. The ethyl is more expensive but has a stronger note. It differs from vanillin by having an ethoxy group (–O–CH<sub>2</sub>CH<sub>3</sub>) instead of a methoxy group (–O–CH<sub>3</sub>).		Vanillin and ] are used by the food industry; ethylvanillin is more expensive, but has a stronger ]. It differs from vanillin by having an ethoxy group (−O−CH<sub>2</sub>CH<sub>3</sub>) instead of a methoxy group (−O−CH<sub>3</sub>).
	Natural "vanilla extract" is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound ]. Today, artificial vanillin is made from either ] or from ], a constituent of ] which is a byproduct of the ].		Natural ] is a mixture of several hundred different compounds in addition to vanillin. Artificial vanilla flavoring is often a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, synthetic preparation of its predominant component has long been of interest. The first commercial synthesis of vanillin began with the more readily available natural compound ] (4-allyl-2-methoxyphenol). Today, artificial vanillin is made either from ] or ].
	Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than oil-based flavoring; the difference is due to the presence of ] in the lignin-derived product, an impurity not found in vanillin synthesized from guaiacol.<ref>According to ], blind taste-testing panels cannot distinguish between the flavors of synthetic vanillin from lignin and from guaicol, but can distinguish the odors of these two types of synthetic vanilla extracts. Guaiacol vanillin, adulterated with acetovanillone, has an odor indistinguishable from lignin vanillin.</ref>		Lignin-based artificial vanilla flavoring is alleged to have a richer flavor profile than that from guaiacol-based artificial vanilla; the difference is due to the presence of ], a minor component in the lignin-derived product that is not found in vanillin synthesized from guaiacol.<ref>According to ], blind taste-testing panels cannot distinguish between the flavors of synthetic vanillin from lignin and those from guaicol, but can distinguish the odors of these two types of synthetic vanilla extracts. Guaiacol vanillin, adulterated with acetovanillone, has an odor indistinguishable from lignin vanillin.</ref>
	== History ==		== Natural history ==
			Although it is generally accepted that vanilla was domesticated in ] and subsequently spread to the ] in the 16th century, in 2019, researchers published a ] stating that vanillin residue had been discovered inside jars within a tomb in ] dating to the 2nd millennium BCE, suggesting the possible cultivation of an unidentified, Old World-endemic '']'' species in ] since the Middle ].<ref>{{Cite journal | url=https://www.sciencedirect.com/science/article/abs/pii/S2352409X18307557 | title=First evidence for vanillin in the old world: Its use as mortuary offering in Middle Bronze Canaan | journal=Journal of Archaeological Science: Reports | date=June 2019 | last1 = Linares | first1 = V. | last2 = Adams | first2 = M.&nbsp;J. | last3 = Cradic | first3 = M.&nbsp;S. | last4 = Finkelstein | first4 = I. | last5 = Lipschits | first5 = O. | last6 = Martin | first6 = M.&nbsp;A.&nbsp;S.| last7 = Neumann | first7 = R. | last8 = Stockhammer | first8 = P.&nbsp;W. | last9 = Gadot | first9 = Y.| volume=25 | pages=77–84 | doi=10.1016/j.jasrep.2019.03.034 | bibcode=2019JArSR..25...77L | s2cid=181608839 }}</ref><ref name=":0b">{{Cite journal | title=Amir A, Finkelstein I, Shalev Y, Uziel J, Chalaf O, Freud L, et al. (2022) Residue analysis evidence for wine enriched with vanilla consumed in Jerusalem on the eve of the Babylonian destruction in 586 BCE. PLoS ONE 17(3)| year=2022| doi=10.1371/journal.pone.0266085| pmid=35349581| doi-access=free| last1=Amir| first1=A.| last2=Finkelstein| first2=I.| last3=Shalev| first3=Y.| last4=Uziel| first4=J.| last5=Chalaf| first5=O.| last6=Freud| first6=L.| last7=Neumann| first7=R.| last8=Gadot| first8=Y.| journal=PLOS ONE| volume=17| issue=3| pages=e0266085| pmc=8963535}}</ref> Traces of vanillin were also found in wine jars in ], which were used by the ] elite before ] in 586&nbsp;BCE.<ref name=":0b" />
	Vanilla was cultivated as a flavoring by pre-Columbian Mesoamerican peoples; at the time of their conquest by ], the ] used it as a flavoring for ]. Europeans became aware of both chocolate and vanilla around 1520.<ref name="#esposito1997|Esposito 1997">]</ref>
			Vanilla beans, called ''tlilxochitl,'' were discovered and cultivated as a flavoring for beverages by native Mesoamerican peoples, most famously the Totonacs of modern-day ], Mexico. Since at least the early 15th century, the ] used vanilla as a flavoring for ] in drinks called ''xocohotl''.<ref>{{Cite web |last=MexicanVanilla.com |title=Mexican Vanilla - A History |url=https://mexicanvanilla.com/pages/history-of-vanilla |access-date=2022-06-14 |website=MexicanVanilla.com |language=en}}</ref>
	Vanillin was first isolated as a relatively pure substance in 1858 by ], who obtained it by evaporating a vanilla extract to dryness, and ] the resulting solids from hot water.<ref>]</ref> In 1874, the German scientists ] and ] deduced its chemical structure, at the same time finding a synthesis for vanillin from ], a ] of ] found in ] bark.<ref>]</ref> Tiemann and Haarmann founded a company, Haarmann & Reimer (now part of ]) and started the first industrial production of Vanillin using their process in ] (Germany). In 1876, ] synthesized vanillin ('''2''') from ] ('''1''').<ref>]</ref>
	{{center|]<br />Synthesis of Vanillin by Reimer}}
	By the late 19th century, semisynthetic vanillin derived from the ] found in ] oil was commercially available.<ref>According to ], synthetic vanillin was sold commercially in 1874, the same year Tiemann and Haarmann's original synthesis was published. Haarmann & Reimer, one of the corporate ancestors of the modern flavor and aroma manufacturer ], was in fact established in 1874. However, ] claims that synthetic vanillin first became available in 1894 when Rhône-Poulenc (since 1998, ]) entered the vanillin business. If the former claim is correct, the authors of the latter article, being employees of Rhône-Poulenc, may have been unaware of any previous vanillin manufacture.</ref>
			== Synthetic history ==
	Synthetic vanillin became significantly more available in the 1930s, when production from ] was supplanted by production from the ]-containing waste produced by the ] for preparing wood pulp for the ] industry. By 1981, a single pulp and paper mill in Ontario supplied 60% of the world market for synthetic vanillin.<ref name="#hocking1997|Hocking 1997">]</ref> However, subsequent developments in the wood pulp industry have made its lignin wastes less attractive as a raw material for vanillin synthesis. While some vanillin is still made from lignin wastes, most synthetic vanillin is today synthesized in a two-step process from the petrochemical precursors ] and ].<ref name="#esposito1997|Esposito 1997"/>
			Vanillin was first isolated as a relatively pure substance in 1858 by ], who obtained it by evaporating a vanilla extract to dryness and ] the resulting solids from hot water.<ref>].</ref> In 1874, the German scientists ] and ] deduced its chemical structure, at the same time finding a synthesis for vanillin from ], a ] of ] found in ] bark.<ref>].</ref> Tiemann and Haarmann founded a company Haarmann and Reimer (now part of ]) and started the first industrial production of vanillin using their process (now known as the ]) in ], Germany. In 1876, ] synthesized vanillin ('''2''') from guaiacol ('''1''').<ref>].</ref>
			]
			By the late 19th century, semisynthetic vanillin derived from the eugenol found in ] was commercially available.<ref>According to ], synthetic vanillin was sold commercially in 1874, the same year Tiemann and Haarmann's original synthesis was published. Haarmann and Reimer, one of the corporate ancestors of the modern flavor and aroma manufacturer Symrise, was in fact established in 1874. However, ] claims that synthetic vanillin first became available in 1894 when Rhône-Poulenc (since 1998, ]) entered the vanillin business. If the former claim is correct, the authors of the latter article, being employees of Rhône-Poulenc, may have been unaware of any previous vanillin manufacture.</ref>
	Beginning in 2000, ] began marketing biosynthetic vanillin prepared by the action of microorganisms on ] extracted from ]. At $700/kg, this product, sold under the trademarked name Rhovanil Natural, is not cost-competitive with petrochemical vanillin, which sells for around $15/kg.<ref>]</ref> However, unlike vanillin synthesized from lignin or guaiacol, it can be labeled as a natural flavoring.
			Synthetic vanillin became significantly more available in the 1930s, when production from clove oil was supplanted by production from the ]-containing waste produced by the ] for preparing wood pulp for the ]. By 1981, a single pulp and paper mill in ], supplied 60% of the world market for synthetic vanillin.<ref name="#hocking1997|Hocking 1997">].</ref> However, subsequent developments in the wood pulp industry have made its lignin wastes less attractive as a raw material for vanillin synthesis. Today, approximately 15% of the world's production of vanillin is still made from lignin wastes,<ref name="Fache et al 2015">]</ref> while approximately 85% is synthesized in a two-step process from the ] precursors ] and ].<ref name="#esposito1997|Esposito 1997">].</ref><ref>{{cite book |author1=Kamlet, Jonas |author2=Mathieson, Olin |name-list-style=amp |title=Manufacture of vanillin and its homologues U.S. Patent 2,640,083 |year=1953 |publisher=U.S. Patent Office |url=https://docs.google.com/viewer?url=patentimages.storage.googleapis.com/pdfs/US2640083.pdf |author1-link=Jonas Kamlet }}</ref>
			Beginning in 2000, ] began marketing biosynthetic vanillin prepared by the action of microorganisms on ] extracted from ]. This product, sold at ]$700/kg under the trademarked name Rhovanil Natural, is not cost-competitive with petrochemical vanillin, which sells for around US$15/kg.<ref>].</ref> However, unlike vanillin synthesized from lignin or guaiacol, it can be labeled as a natural flavoring.
	== Occurrence ==		== Occurrence ==
	]		]
	Vanillin is most prominent as the principal flavor and aroma compound in vanilla. Cured vanilla pods contain approximately 2% by dry weight vanillin; on cured pods of high quality, relatively pure vanillin may be visible as a white dust or "frost" on the exterior of the pod.		Vanillin is most prominent as the principal flavor and aroma compound in ]. Cured vanilla pods contain about 2% by dry weight vanillin. Relatively pure vanillin may be visible as a white dust or "frost" on the exteriors of cured pods of high quality.
			It is also found in '']'', a species of orchid native to Paraguay and southern Brazil,<ref name= floralibrary>{{cite web |url=http://www.floralibrary.com/flora/leptotes/bicolor |title=Leptotes bicolor|publisher=Flora Library |access-date=2011-08-21}}</ref> and the ].
	At lower concentrations, vanillin contributes to the flavor and aroma profiles of foodstuffs as diverse as ],<ref>]</ref> ],<ref>]</ref> ]<ref>]</ref> and ]<ref>]</ref> fruits. Aging in ] barrels imparts vanillin to some ]s and ]s.<ref>]</ref> In other foods, heat treatment evolves vanillin from other chemicals. In this way, vanillin contributes to the flavor and aroma of ],<ref>]</ref> ],<ref>]</ref> and ] products including corn ]s<ref>]</ref> and ].<ref>]</ref>
			At lower concentrations, vanillin contributes to the flavor and aroma profiles of foodstuffs as diverse as ],<ref>].</ref> ],<ref>].</ref> ],<ref>].</ref> and ]<ref>].</ref> fruits.
	== Production ==
	=== Natural production ===
	Natural vanillin is extracted from the seed pods of ''] planifola'', a ] ] native to Mexico, but now grown in tropical areas around the globe. ] is presently the largest producer of natural vanillin.
			Aging in ] imparts vanillin to some ]s, ],<ref>{{cite journal | doi = 10.1007/BF01192948 | volume=199 | title=Analysis of polyphenolic compounds of different vinegar samples | year=1994 | journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung | pages=29–31 | last1 = Carrero Gálvez| first1 = Miguel | s2cid=91784893 }}.</ref> and ]s.<ref>].</ref>
	As harvested, the green seed pods contain vanillin in the form of its β-D-]; the green pods do not have the flavor or odor of vanilla.<ref>]</ref>
	{{center|]<br />β-D-glycoside of vanillin}}
			In other foods, heat treatment generates vanillin from other compounds. In this way, vanillin contributes to the flavor and aroma of ],<ref>{{Cite journal | doi = 10.1002/ffj.2730100102 | title = Determination of potent odourants in roasted coffee by stable isotope dilution assays | year = 1995 | last1 = Semmelroch | first1 = P. | last2 = Laskawy | first2 = G. | last3 = Blank | first3 = I. | last4 = Grosch | first4 = W. | journal = Flavour and Fragrance Journal | volume = 10 | pages = 1–7}}</ref><ref>].</ref> ],<ref>].</ref> and ] products, including corn ]s<ref>].</ref> and ].<ref>].</ref>
			==Chemistry==
			===Natural production===
			Natural vanillin is extracted from the seed pods of '']'', a ] ] native to Mexico, but now grown in tropical areas around the globe. ] is presently the largest producer of natural vanillin.
			], the β-{{sc|D}}-glucoside of vanillin]]
			As harvested, the green seed pods contain vanillin in the form of ], its β-{{sc|D}}-]; the green pods do not have the flavor or odor of vanilla.<ref name = walton>].</ref> Vanillin is released from glucovanillin by the action of the enzyme ] during ripening<ref>{{cite journal | doi = 10.1111/j.1365-2621.1943.tb18011.x | title = ACTION OF a β-GLUCOSIDASE IX THE CURING OF VANILLA | date = 1943 | last1 = Arana | first1 = Francisca E. | journal = Journal of Food Science | volume = 8 | issue = 4 | pages = 343–351 }}</ref><ref>{{cite journal | title = Changes in vanillin and glucovanillin concentrations during the various stages of the process traditionally used for curing Vanilla fragrans beans in Reunion | author = Odoux, Eric | date = 2000 | journal = Fruits | volume = 55 | issue = 2 | pages = 119–125 }}</ref> and during the curing process.<ref>{{cite journal | doi = 10.1021/jf00058a019 | title = Determination of Glucovanillin and Vanillin in Cured Vanilla Pods | date = 1995 | last1 = Voisine | first1 = Richard | last2 = Carmichael | first2 = Lucie | last3 = Chalier | first3 = Pascale | last4 = Cormier | first4 = Francois | last5 = Morin | first5 = Andre | journal = Journal of Agricultural and Food Chemistry | volume = 43 | issue = 10 | pages = 2658–2661 | bibcode = 1995JAFC...43.2658V }}</ref>
	After being harvested, their flavor is developed by a months-long curing process, the details of which vary among vanilla-producing regions, but in broad terms it proceeds as follows:		After being harvested, their flavor is developed by a months-long curing process, the details of which vary among vanilla-producing regions, but in broad terms it proceeds as follows:
	First, the seed pods are ] in hot water, to arrest the processes of the living plant tissues. Then, for 1&ndash;2 weeks, the pods are alternately sunned and sweated: during the day, they are laid out in the sun, and each night, wrapped in cloth and packed in airtight boxes to sweat. During this process, the pods become a dark brown, and ]s in the pod release vanillin as the free molecule. Finally, the pods are dried and further aged for several months, during which time their flavors further develop. Several methods have been described for curing vanilla in days rather than months, although they have not been widely developed in the natural vanilla industry,<ref>] reviews several such proposed innovations in vanilla processing, including processes in which the seed pods are chopped, frozen, warmed by a heat source other than the sun, or crushed and treated by various enzymes. Whether or not these procedures produce a product whose taste is comparable to traditionally prepared natural vanilla, many of them are incompatible with the customs of the natural vanilla market, in which the vanilla beans are sold whole, and graded by, among other factors, their length.</ref> with its focus on producing a premium product by established methods, rather than on innovations that might alter the product's flavor profile.		First, the seed pods are ] in hot water, to arrest the processes of the living plant tissues. Then, for 1–2 weeks, the pods are alternately sunned and sweated: during the day they are laid out in the sun, and each night wrapped in cloth and packed in airtight boxes to sweat. During this process, the pods become dark brown, and ]s in the pod release vanillin as the free molecule. Finally, the pods are dried and further aged for several months, during which time their flavors further develop. Several methods have been described for curing vanilla in days rather than months, although they have not been widely developed in the natural vanilla industry,<ref>] reviews several such proposed innovations in vanilla processing, including processes in which the seed pods are chopped, frozen, warmed by a heat source other than the sun, or crushed and treated by various enzymes. Whether or not these procedures produce a product whose taste is comparable to traditionally prepared natural vanilla, many of them are incompatible with the customs of the natural vanilla market, in which the vanilla beans are sold whole, and graded by, among other factors, their length.</ref> with its focus on producing a premium product by established methods, rather than on innovations that might alter the product's flavor profile.
			===Biosynthesis===
	Vanillin accounts for about 2% of the dry weight of cured vanilla beans, and is the chief among about 200 other flavor compounds found in vanilla.
			]
	=== Biosynthesis ===
			Although the exact route of vanillin biosynthesis in ''V.&nbsp;planifolia'' is currently unknown, several pathways are proposed for its biosynthesis. Vanillin biosynthesis is generally agreed to be part of the ] starting with {{sc|L}}-phenylalanine,<ref name="digital.library.unt.edu">{{cite journal | last1 = Dixon | first1 = R.&nbsp;A. | title = Vanillin Biosynthesis – Not as simple as it seems? | url = https://digital.library.unt.edu/ark:/67531/metadc279692/m2/1/high_res_d/Dixon%20vanillin%202011.pdf | journal = Handbook of Vanilla Science and Technology | year = 2014 | page = 292 }}</ref> which is deaminated by ] (PAL) to form t-]. The para position of the ring is then ]d by the ] enzyme cinnamate 4-hydroxylase (C4H/P450) to create ''p''-].<ref name="nature.com">{{cite journal | last1 = Gallage | first1 = N.&nbsp;J. | last2 = Hansen | first2 = E.&nbsp;H. | last3 = Kannangara | first3 = R. | last4 = Olsen | first4 = E.&nbsp;C. | last5 = Motawia | first5 = M.&nbsp;S. | last6 = Jørgensen | first6 = K. | last7 = Holme | first7 = I. | last8 = Hebelstrup | first8 = K. | last9 = Grisoni | first9 = M. | last10 = Møller | first10 = L.&nbsp;B. | title = Vanillin formation from ferulic acid in ''Vanilla planifolia'' is catalysed by a single enzyme | journal = Nature Communications | year = 2014 | volume = 5 | page = 4037 | doi = 10.1038/ncomms5037 | pmid=24941968 | pmc=4083428| bibcode = 2014NatCo...5.4037G }}</ref> Then, in the proposed ferulate pathway, 4-hydroxycinnamoyl-CoA ligase (4CL) attaches ''p''-coumaric acid to ] (CoA) to create ''p''-coumaroyl CoA. ] (HCT) then converts ''p''-coumaroyl CoA to 4-coumaroyl ]/]. This subsequently undergoes oxidation by the P450 enzyme coumaroyl ester 3’-hydroxylase (C3’H/P450) to give caffeoyl shikimate/quinate. HCT then exchanges the shikimate/quinate for CoA to create caffeoyl CoA, and 4CL removes CoA to afford caffeic acid. Caffeic acid then undergoes ] by caffeic acid O-] (COMT) to give ferulic acid. Finally, vanillin synthase hydratase/lyase (vp/VAN) catalyzes hydration of the double bond in ferulic acid followed by a retro-aldol elimination to afford vanillin.<ref name="nature.com"/> Vanillin can also be produced from vanilla glycoside with the additional final step of deglycosylation.<ref name = walton/> In the past ''p''-hydroxybenzaldehyde was speculated to be a precursor for vanillin biosynthesis. However, a 2014 study using ] ] indicated that ''p''-hydroxybenzaldehyde is not used to synthesise vanillin or vanillin glucoside in the vanilla orchids.<ref name="nature.com" />
	The biosynthesis of vanillin is achieved by the conversion of tyrosine into 4-coumaric acid then into ferulic acid and finally into vanillin. Vanillin is then converted into its corresponding glucose ester.
			===Chemical synthesis===
	]
			The demand for vanilla flavoring has long exceeded the supply of vanilla beans. {{As of|2001}}, the annual demand for vanillin was 12,000 tons, but only 1,800 tons of natural vanillin were produced.<ref>].</ref> The remainder was produced by ]. Vanillin was first synthesized from eugenol (found in oil of clove) in 1874–75, less than 20 years after it was first identified and isolated. Vanillin was commercially produced from eugenol until the 1920s.<ref>]. This chemical process can be conveniently carried out on the laboratory scale using the procedure described by ].</ref> Later it was synthesized from lignin-containing "brown liquor", a byproduct of the ] for making ].<ref name="#hocking1997|Hocking 1997"/> Counterintuitively, though it uses waste materials, the lignin process is no longer popular because of environmental concerns, and today most vanillin is produced from ].<ref name="#hocking1997|Hocking 1997"/> Several routes exist for synthesizing vanillin from guaiacol.<ref>].</ref>
			At present, the most significant of these is the two-step process practiced by ] since the 1970s, in which guaiacol ('''1''') reacts with ] by ].<ref>{{cite journal |author1=Fatiadi, Alexander |author2=Schaffer, Robert |name-list-style=amp |title=An Improved Procedure for Synthesis of {{sc|DL}}-4-Hydroxy-3-methoxymandelic Acid ({{sc|DL}}-"Vanillyl"-mandelic Acid, VMA) |journal=Journal of Research of the National Bureau of Standards Section A |year=1974 |volume=78A |issue=3 |pages=411–412 |doi=10.6028/jres.078A.024|pmid=32189791 |pmc=6742820 |doi-access=free }}</ref> The resulting ] ('''2''') is then converted by 4-Hydroxy-3-methoxyphenylglyoxylic acid ('''3''') to vanillin ('''4''') by oxidative decarboxylation.<ref name="#esposito1997|Esposito 1997"/>
	The conversion of ferulic acid into vanillin is achieved by conversion of the carboxylic acid into a thioester with acetyl-CoA. The feruloyl CoA is then hydrated into 4-hydroxy-3-methoxyphenyl-β-hydroxyprpionyl CoA (HMPHP CoA). At this point, two different pathways have been purposed for the conversion of HMPHP CoA into vanillin. One pathway is similar to the β-oxidation of fatty acid, beginning with the oxidation of the hydroxyl group, cleavage to release acetyl-CoA to form a shortened thioester and then cleavage of the thioester into an aldehyde. The other pathway contains one enzyme that would simultaneously oxidize the hydroxyl group along with the release of aceyl-CoA.
	:]		: ]
			===Wood-based vanillin===
	=== Chemical synthesis ===
			15% of the world's production of vanillin is produced from ], a byproduct from the manufacture of ] via the ].<ref name="#hocking1997|Hocking 1997"/><ref name="Fache et al 2015"/> The sole producer of wood-based vanillin is the company ] located in ], ].
	The demand for vanilla flavoring has long exceeded the supply of vanilla beans. {{As of|2001}}, the annual demand for vanillin was 12,000 tons, but only 1,800 tons of natural vanillin were produced.<ref>]</ref> The remainder was produced by ]. Vanillin was first synthesized from ] (found in oil of ]) in 1874–75, less than 20 years after it was first identified and isolated. Vanillin was commercially produced from eugenol until the 1920s.<ref>]. This chemical process can be conveniently carried out on the laboratory scale using the procedure described by ].</ref> Later it was synthesized from ]-containing "brown liquor", a byproduct of the ] for making ].<ref name="#hocking1997|Hocking 1997"/> Counter-intuitively, even though it uses waste materials, the lignin process is no longer popular because of environmental concerns, and today most vanillin is produced from the ] raw material ].<ref name="#hocking1997|Hocking 1997"/> Several routes exist for synthesizing vanillin from guaiacol.<ref>]</ref>
			Wood-based vanillin is produced by copper-catalyzed oxidation of the ] structures in ] under alkaline conditions<ref>]</ref> and is claimed by the manufacturing company to be preferred by their customers due to, among other reasons, its much lower carbon footprint than petrochemically synthesized vanillin.
	At present, the most significant of these is the two-step process practiced by ] since the 1970s, in which guaiacol ('''1''') reacts with ] by ]. The resulting ] ('''2''') is then converted via 4-Hydroxy-3-methoxyphenylglyoxylic acid ('''3''') to vanillin ('''4''') by oxidative decarboxylation.<ref name="#esposito1997|Esposito 1997"/>
	:]
			===Fermentation===
	In October 2007 Mayu Yamamoto of the International Medical Center of Japan won an ] for developing a way to extract vanillin from cow dung.<ref></ref>
			The company Evolva has developed a genetically modified microorganism which can produce vanillin. Because the microbe is a ], the resulting vanillin would not fall under U.S. GMO labeling requirements, and because the production is nonpetrochemical, food using the ingredient can claim to contain "no artificial ingredients".<ref>{{Cite web|last=Bomgardner|first=Melody M.|date=2016-09-14|title=The Problem with Vanilla|url=https://www.scientificamerican.com/article/the-problem-with-vanilla/|access-date=2020-10-19|website=Scientific American|language=en}}</ref>
			Using ] as an input and a specific non GMO species of '']'' bacteria, natural vanillin can be produced.
			===Biochemistry===
			Several studies have suggested that vanillin can affect the performance of ] ].<ref>{{cite journal |last1=Brochado|first1=Ana|date=4 July 2018|title=Species-specific activity of antibacterial drug combinations|journal=]|volume=559|issue=7713|pages=259–263|doi=10.1038/s41586-018-0278-9|pmid=29973719|pmc=6219701|bibcode=2018Natur.559..259B}}</ref><ref>{{cite journal |last1=Bezzera|first1=Camila|date=1 December 2017|title=Vanillin selectively modulates the action of antibiotics against resistant bacteria.|journal=Microbial Pathogenesis|volume=113|pages=265–268|doi=10.1016/j.micpath.2017.10.052|pmid=29107747}}</ref>
	== Uses ==		== Uses ==
	]		]
	The largest use of vanillin is as a flavoring, usually in ] foods. The ] and ] industries together comprise 75% of the market for vanillin as a flavoring, with smaller amounts being used in ]s and ].<ref>], p. 33</ref>		The largest use of vanillin is as a flavoring, usually in ] foods. The ] and ] industries together comprise 75% of the market for vanillin as a flavoring, with smaller amounts being used in ]s and ].<ref>], p. 33.</ref>
			Vanillin is also used in the fragrance industry, in ]s, and to mask unpleasant odors or tastes in medicines, livestock ], and cleaning products.<ref name="#esposito1997|Esposito 1997"/> It is also used in the flavor industry, as a very important key note for many different flavors, especially creamy profiles such as ].
			Additionally, vanillin can be used as a general-purpose stain for visualizing spots on ] plates. This stain yields a range of colors for these different components.
			] can be used to visualize the localisation of tannins in cells.
			Vanillin is becoming a popular choice for the development of bio-based plastics.<ref>{{cite journal |doi = 10.1016/j.eurpolymj.2015.03.050 |year = 2015 |title= Vanillin, a key-intermediate of biobased polymers |journal = European Polymer Journal |volume=68 |pages=488–502 |last1=Fache |first1=Maxence |last2=Boutevin |first2=Bernard |last3=Caillol |first3=Sylvain|bibcode = 2015EurPJ..68..488F }}</ref>
			===Manufacturing===
			Vanillin has been used as a chemical intermediate in the production of ], ], and other ].<ref>{{cite journal |pmid=17886091 |year=2008 |last1=Sinha |first1=A. K. |title=A comprehensive review on vanilla flavor: Extraction, isolation and quantification of vanillin and others constituents |journal=International Journal of Food Sciences and Nutrition |volume=59 |issue=4 |pages=299–326 |last2=Sharma |first2=U. K. |last3=Sharma |first3=N. |doi=10.1080/09687630701539350|s2cid=37559260 }}</ref> In 1970, more than half the world's vanillin production was used in the synthesis of other chemicals.<ref name="#hocking1997|Hocking 1997"/> As of 2016, vanillin uses have expanded to include ]s, flavoring and aromatic masking in medicines, various consumer and cleaning products, and ] foods.<ref>{{cite web |url=http://www.prnewswire.com/news-releases/global-vanillin-market-research-report---industry-analysis-size-share-growth-trends-and-forecast-2015---2022-300328321.html |title=Global Vanillin Market Research Report – Industry Analysis, Size, Share, Growth, Trends and Forecast 2015–2022 |date=14 September 2016 |publisher=PRNewsire |access-date=18 February 2017}}</ref>
			== Adverse effects ==
			Vanillin can trigger ]s in a small fraction of the people who experience migraines.<ref name="Saint Denis-1996">{{Cite journal | author= Saint Denis, M. | author2 = Coughtrie, M. W. | author3 = Guilland, J. C. | author4 = Verges, B. | author5 = Lemesle, M. | author6 = Giroud, M. | title = Migraine induced by vanillin | journal = Presse Méd. | volume = 25 | issue = 40 | pages = 2043 |date=Dec 1996 | pmid = 9082382}}</ref>
			Some people have ] to vanilla.<ref>{{cite journal | pmc = 1245616 | date = 1987 | last1 = Van Assendelft | first1 = A. H. | title = Adverse drug reactions checklist | journal = British Medical Journal (Clinical Research Ed.) | volume = 294 | issue = 6571 | pages = 576–577 | doi = 10.1136/bmj.294.6571.576-d | pmid = 3103791 }}</ref> They may be allergic to synthetically produced vanilla but not to natural vanilla, or the other way around, or to both.<ref name=":0a">{{Cite book|last1=Rietschel|first1=Robert L.|url=https://books.google.com/books?id=dQBAzfyCeQ8C&q=vanillin+allergy&pg=PA444|title=Fisher's Contact Dermatitis|last2=Fowler|first2=Joseph F.|last3=Fisher|first3=Alexander A.|date=2008|publisher=PMPH-USA|isbn=978-1-55009-378-0|pages=444|language=en}}</ref>
	Vanillin is also used in the fragrance industry, in ]s, and to mask unpleasant odors or tastes in medicines, livestock ], and cleaning products.<ref name="#esposito1997|Esposito 1997"/> It is also used in the flavor industry, as a very important key note for many different flavors, specially creamy profiles.
			Vanilla orchid plants can trigger ], especially among people working in the vanilla trade if they come into contact with the plant's sap.<ref name=":0a" /> An allergic contact dermatitis called vanillism produces swelling and redness, and sometimes other symptoms.<ref name=":0a" /> The sap of most species of vanilla orchid which exudes from cut stems or where beans are harvested can cause moderate to severe dermatitis if it comes in contact with bare skin. The sap of vanilla orchids contains ] crystals, which are thought to be the main causative agent of contact dermatitis in vanilla plantation workers.<ref>{{cite web|url=http://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:262578-2|title=Vanilla planifolia Andrews - Plants of the World Online - Kew Science|website=powo.science.kew.org|url-status=live|archive-url=https://web.archive.org/web/20171122013549/http://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:262578-2|archive-date=22 November 2017|df=dmy-all}}</ref><ref>{{PFAF |url-status=live |archive-url=https://web.archive.org/web/20171201033211/http://pfaf.org/user/Plant.aspx?LatinName=Vanilla+planifolia |archive-date=1 December 2017 |df=dmy-all}}</ref>
	Vanillin has been used as a chemical intermediate in the production of ] and other ]. In 1970, more than half the world's vanillin production was used in the synthesis of other chemicals,<ref name="#hocking1997|Hocking 1997"/> but as of 2004 this use accounts for only 13% of the market for vanillin.<ref>], p. 32.</ref>
			A ] called vanilla lichen can be caused by ]s (''Tyroglyphus farinae'').<ref name=":0a" />
	Additionally, vanillin can be used as a general purpose stain for developing ] (TLC) plates to aid in visualizing components of a reaction mixture. This stain yields a range of colors for these different components.
	==Adverse effects==		== Ecology ==
			'']'', one of the vectors of the ], uses vanillin as a signal to find a host tree during ].<ref>{{cite journal|title = Vanillin and Syringaldehyde as Attractants for Scolytus multistriatus (Coleoptera: Scolytidae)|last1= Meyer|first1=H.J.|last2= Norris|first2=D.M.|journal= Annals of the Entomological Society of America|date= 17 July 1967| volume= 60|number= 4| pages= 858–859 |doi = 10.1093/aesa/60.4.858}}</ref>
	Vanillin can trigger ]s in a small fraction of the people who experience migraines.<ref name="Saint Denis-1996">{{Cite journal | author= Saint Denis, M. | author2 = Coughtrie, MW. | author3 = Guilland, JC. | author4 = Verges, B. | author5 = Lemesle, M. | author6 = Giroud, M. | title = . | journal = Presse Med | volume = 25 | issue = 40 | pages = 2043 | month = Dec | year = 1996 | doi = | PMID = 9082382 }}</ref>
	== See also ==		== See also ==
	*]		* ]
			* Other ]s:
			** ]
			** ]
			** ]
			** ]
			* ]
			* ]
			* ]
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	| journal = ]		| journal = ]
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			}}
	{{refend}}		{{refend}}
	==Notes==		== Notes ==
			{{reflist}}
			{{Transient receptor potential channel modulators}}
	{{reflist|2}}
			{{Authority control}}
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	{{Link GA|de}}
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