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{{Chembox {{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 456020587 | verifiedrevid = 459981878
| ImageFile = Brazilin.png | ImageFile = Brazilin.svg
| ImageSize = 200px | ImageSize = 170
| ImageAlt = Skeletal formula of brazilin
⚫ | IUPACName = (6a''S'',11b''R'')-7,11b-Dihydro-6''H''-indenochromene-3,6a,9,10-tetrol
| ImageFile1 = Brazilin 3D spacefill.png
⚫ | OtherNames = Brasilin; Natural Red 24
| ImageSize1 = 210
⚫ | Section1 = {{Chembox Identifiers
| ImageAlt1 = Space-filling model of the brazilin molecule
⚫ | PIN = (6a''S'',11b''R'')-7,11b-Dihydroindenobenzopyran-3,6a,9,10(6''H'')-tetrol
⚫ | OtherNames = Brasilin; Natural Red 24; CI 75280
⚫ |Section1={{Chembox Identifiers
| Beilstein = 4198570
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 66104 | ChemSpiderID = 66104
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | InChI = 1/C16H14O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,15,17-20H,6-7H2/t15-,16+/m0/s1
⚫ | InChIKey = UWHUTZOCTZJUKC-JKSUJKDBBS
⚫ | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 598951 | ChEMBL = 598951
| EINECS = 207-477-6
| KEGG = C09920
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 474-07-7
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FZ39SW1K10
⚫ | PubChem = 73384
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 3170
| SMILES1 = Oc1cc3c(cc1O)2c4c(OC2(O)C3)cc(O)cc4 | SMILES1 = Oc1cc3c(cc1O)2c4c(OC2(O)C3)cc(O)cc4
⚫ | InChI = 1/C16H14O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,15,17-20H,6-7H2/t15-,16+/m0/s1
⚫ | InChIKey = UWHUTZOCTZJUKC-JKSUJKDBBS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H14O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,15,17-20H,6-7H2/t15-,16+/m0/s1 | StdInChI = 1S/C16H14O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,15,17-20H,6-7H2/t15-,16+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UWHUTZOCTZJUKC-JKSUJKDBSA-N | StdInChIKey = UWHUTZOCTZJUKC-JKSUJKDBSA-N
⚫ | CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 474-07-7 -->
⚫ | PubChem = 73384
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 3170
| SMILES = C1C2=CC(=C(C=C231(COC4=C3C=CC(=C4)O)O)O)O | SMILES = C1C2=CC(=C(C=C231(COC4=C3C=CC(=C4)O)O)O)O
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=16 | H=14 |O=5 | C=16 | H=14 | O=5
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}

'''Brazilin''' is a red pigment obtained from the wood of the ] family (''Caesalpinia sp''), and is also known as '''Natural Red 24'''. Brazilin has been used since at least the Middle Ages to ] fabric, and has been used to make paints and inks as well. The specific color produced by the pigment depends on its manner of preparation: in an acidic solution brazilin will appear yellow, but in an alkaline preparation it will appear red. Brazilin is closely related to the blue-black dye ], having one less hydroxyl group. Brazilein is the name for the oxidised pigment<ref></ref>.
'''Brazilin''' is a naturally occurring, ], red ] obtained from the wood of '']'', '']'', ''Caesalpinia violacea'', and '']'' (also known as '''Natural Red 24''' and ''' CI 75280''').<ref name="Dapson and Bain, 2015">{{cite journal| author=Dapson RW, Bain CL| title=Brazilwood, sappanwood, brazilin and the red dye brazilein: from textile dyeing and folk medicine to biological staining and musical instruments. | journal=Biotech Histochem | year= 2015 | volume= 90 | issue= 6 | pages= 401–23 | pmid=25893688 | doi=10.3109/10520295.2015.1021381 | url=https://pubmed.ncbi.nlm.nih.gov/25893688 }} </ref> Brazilin has been used since at least the Middle Ages to ] fabric, and has been used to make paints and inks as well. The specific color produced by the pigment depends on its manner of preparation: in an ] solution brazilin will appear yellow, but in an ] preparation it will appear red. Brazilin is closely related to the blue-black dye precursor ], having one fewer hydroxyl group. Brazilein, the active dye agent, is an oxidized form of brazilin.<ref>{{cite journal | doi = 10.1016/S0924-2031(01)00138-2 | title = Vibrational spectroscopic study of brazilin and brazilein, the main constituents of brazilwood from Brazil | year = 2002 | last1 = De Oliveira | first1 = Luiz F.C. | last2 = Edwards | first2 = Howell G.M. | last3 = Velozo | first3 = Eudes S. | last4 = Nesbitt | first4 = M. | journal = Vibrational Spectroscopy | volume = 28 | issue = 2 | pages = 243}}</ref><ref name="Dapson and Bain, 2015" />


==Sources of brazilin== ==Sources of brazilin==
Many members of the genus ''Caesalpinia'' produce brazilin, including ] (''C. echinata'') and ] (''C. sappan''). The sappanwood is found in India, Malaysia, and Sri Lanka, the latter being a major supplier of the wood to Europe during the early Middle Ages. Later, discovery of brazilwood in the new world led to its rise in popularity with the dye industry and eventually its ]. Brazilwood is now classified as an ]. Brazilin is obtained from the wood of '']'', '']'' (Sappanwood), ''Caesalpinia violacea'', and '']''.<ref name="Dapson and Bain, 2015">{{cite journal| author=Dapson RW, Bain CL| title=Brazilwood, sappanwood, brazilin and the red dye brazilein: from textile dyeing and folk medicine to biological staining and musical instruments. | journal=Biotech Histochem | year= 2015 | volume= 90 | issue= 6 | pages= 401–23 | pmid=25893688 | doi=10.3109/10520295.2015.1021381 | url=https://pubmed.ncbi.nlm.nih.gov/25893688 }} </ref> The sappanwood is found in ], ], ] and ], the latter being a major supplier of the wood to Europe during the early Middle Ages. Later, discovery of ] in the new world led to its rise in popularity with the dye industry and eventually its ]. Brazilwood is now classified as an ].<ref>{{Cite iucn | author = Varty, N. | title = ''Caesalpinia echinata'' | volume = 1998 | page = e.T33974A9818224 | date = 1998 | doi = 10.2305/IUCN.UK.1998.RLTS.T33974A9818224.en }}</ref>


==Extraction and preparation== ==Extraction and preparation==
{{unreferenced section|date=November 2021}}
There are many ways to extract and prepare brazilin. A common recipe, developed in the Middle Ages, is to first powder the brazilwood, turning it into sawdust. Then, the powder can be soaked in ] (which produces a deep, purplish red) or a hot solution of ] (which produces an orange-red color), either of which extracts the color better than plain water alone. To the lye extract, alum is added (or to the alum extract, lye) in order to fix the color, which will precipitate from the solution. The precipitate can be dried and powdered, and is a type of ]. There are many ways to extract and prepare brazilin. A common recipe, developed in the Middle Ages, is to first powder the brazilwood, turning it into sawdust. Then, the powder can be soaked in ] (which produces a deep, purplish red) or a hot solution of ] (which produces an orange-red color), either of which extracts the color better than plain water alone. To the lye extract, alum is added (or to the alum extract, lye) in order to fix the color, which will precipitate from the solution. The precipitate can be dried and powdered, and is a type of ].


Like many lake pigments, the exact colors produced depends on the pH of the mixture and the fixative used. Aluminum mordants used with brazilin produce the standard red colors, while the use of a tin mordant, in the form of SnCl<sub>2</sub> or SnCl<sub>4</sub> added to the extract is capable of yielding a pink color. Like many lake pigments, the exact colors produced depends on the pH of the mixture and the fixative used. Aluminium mordants used with brazilin produce the standard red colors, while the use of a tin mordant, in the form of {{chem|Sn|Cl|2}} or {{chem|Sn|Cl|4}} added to the extract is capable of yielding a pink color.


An alternative preparation which produces a transparent red color involves soaking the brazilwood powder in ] or a solution of ]. Alum is added to help develop and fix the color, which can then be used as a transparent ink or paint. An alternative preparation which produces a transparent red color involves soaking the brazilwood powder in ] or a solution of ]. Alum is added to help develop and fix the color, which can then be used as a transparent ink or paint.


As with ], brazilin can be used for staining cell nuclei in histological preparations when combined with aluminum. The nuclei are then colored red instead of blue. As with ], brazilin can be used for staining cell nuclei in histological preparations when combined with aluminium. The nuclei are then colored red instead of blue.

==Notes==
⚫ {{reflist}}


==References== ==References==
{{nofootnotes|date=September 2012}}
* The Merck Index, 12th Edition. 1392 * The Merck Index, 12th Edition. 1392
* {{cite journal|first=Wayne P.|last=Armstrong|title=Natural Dyes|journal=HerbalGram|year=1994|volume=32|pages=30}} * {{cite journal|first=Wayne P.|last=Armstrong|title=Natural Dyes|journal=HerbalGram|year=1994|volume=32|pages=30}}
* Thompson, Daniel V. ''The Materials and Techniques of Medieval Painting'', Dover Publications, Inc. New York, NY. 1956. * Thompson, Daniel V. ''The Materials and Techniques of Medieval Painting'', Dover Publications, Inc. New York, NY. 1956.
⚫ {{reflist}}


==External links== ==External links==
* *
* *
* {{cite web|last=Poliakoff|first=Martyn|title=Brazilwood Trees & Natural Red 24|url=http://www.periodicvideos.com/videos/feature_brazil_natural_red.htm|work=]|publisher=]|author-link=Martyn Poliakoff}}

{{Dyeing}} {{Dyeing}}
{{Homoisoflavonoids}}


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