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{{Short description|Chemical compound}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 455290378 |
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| verifiedrevid = 458641115 |
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| Name = Borneol |
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| Name = Borneol |
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| ImageFileL1 = Borneol with H.svg |
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| ImageFileL1 = Borneol.svg |
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| ImageSizeL1 = 120px |
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| ImageSizeL1 = 140px |
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| ImageNameL1 = Borneol |
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| ImageFileR1 = Borneol-3D-balls.png |
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| ImageFileR1 = (-)-Borneol.svg |
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| ImageSizeR1 = 140px |
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| ImageSizeR1 = 140px |
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| ImageFileL2 = (+)-borneol-based-on-xtal-3D-bs-17.png |
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| IUPACName = ''endo''-1,7,7-Trimethyl- bicycloheptan-2-ol |
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| ImageNameL2 = (+)-Borneol |
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| Section1 = {{Chembox Identifiers |
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| ImageSizeL2 = 140px |
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| ImageFileR2 = (−)-borneol-based-on-xtal-3D-bs-17.png |
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| ImageNameR2 = (-)-Borneol |
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| ImageSizeR2 = 140px |
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| ImageCaption = (+)-Borneol (left images) and (-)-borneol (right) |
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| IUPACName = ''rel''-(1''R'',2''S'',4''R'')-1,7,7-Trimethylbicycloheptan-2-ol |
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| OtherNames = 1,7,7-Trimethylbicycloheptan-2-''endo''-ol<br>''endo''-2-Bornanol, Borneo camphor |
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| SystematicName = |
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| Section1 = {{Chembox Identifiers |
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| IUPHAR_ligand = 6413 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5026296 |
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| ChemSpiderID = 5026296 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 486208 |
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| ChEMBL = 486208 |
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| PubChem = 6552009 |
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| PubChem = 6552009 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DTGKSKDOIYIVQL-WEDXCCLWSA-N |
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| StdInChIKey = DTGKSKDOIYIVQL-WEDXCCLWSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 507-70-0 |
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| CASNo = 507-70-0 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Comment = (''+''/''-'') |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C01411 |
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| KEGG = C01411 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 15393 |
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| ChEBI = 15393 |
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| EC_number = 207-352-6 |
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| UNNumber = 1312 |
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| SMILES = O1C2CC1(C)C2(C)C |
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| SMILES = O1C2CC1(C)C2(C)C |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=10|H=18|O=1 |
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| C=10 | H=18 | O=1 |
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| Appearance = colorless to white lumps |
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| Density = 1.011 g/cm<sup>3</sup> @ 20 °C |
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| Odor = pungent, ]-like |
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| Density = 1.011 g/cm<sup>3</sup> (20 °C)<ref name=CRC>{{RubberBible86th|page=3.56}}</ref> |
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| MeltingPtC = 208 |
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| MeltingPtC = 208 |
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| BoilingPt = 213 °C |
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| BoilingPtC = 213 |
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| Solubility = slightly soluble (<small>D</small>-form) |
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}} |
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| SolubleOther = soluble in ], ], ], ], ], ], ], ] |
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| Section3 = {{Chembox Hazards |
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| MagSus = {{val|-1.26|e=-4|u=cm<sup>3</sup>/mol}} }} |
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| ExternalMSDS = |
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| Section3 = {{Chembox Hazards |
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| GHSPictograms = {{GHS02}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|228}} |
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| PPhrases = {{P-phrases|210|240|241|280|370+378}} |
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| NFPA-H = 2 | NFPA-F = 2 | NFPA-R = 0 |
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| FlashPtC = 65 |
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| ExternalSDS = |
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}} |
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}} |
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| Section4 = |
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| Section8 = {{Chembox Related |
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| Section5 = |
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| OtherCpds = ] (hydrocarbon) |
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| Section6 = |
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| Section8 = {{Chembox Related |
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| OtherCompounds = ] (hydrocarbon) |
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}} |
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}} |
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}} |
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}} |
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'''Borneol''' is a ] ] and a ] derivative. The ] group in this compound is placed in an '']'' position. The exo diastereomer is called ]. Being chiral, borneol exists as ]s, both of which are found in nature: ''d''-borneol (also written (+)-borneol) and ''l''-borneol (or (−)-borneol). |
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==Reactions == |
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'''Borneol''' is a ] ] and a ]. The ] group in this compound is placed in an ] position. |
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Borneol is ] to the ] (]). |
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==Occurrence == |
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Borneol is easily ] to the ] yielding ]. One historical name for borneol is '''Borneo camphor''' which explains the name. Borneol can be synthesized by ] of ] by the ]. The same reduction but then fast and irreversible with ] gives ] as the ] reaction product. |
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The compound was named in 1842 by the French chemist ].<ref>{{cite journal|first=C. |last=Gerhardt |date=1842 |title=Sur la transformation de l'essence de valériane en camphre de Bornéo et en camphre des laurinées |trans-title=On the transformation of the essence of valerian into Borneo camphor and into laurel camphor |journal=Comptes rendus |volume=14 |page=832–835}}<br>: ''"Je donne, par cette raison, à l'hydrogène carboné de l'essence de valériane, le nom de ''bornéène'', et, au camphre lui-même, celui de ''bornéol''."'' (I give, for this reason , to the hydrocarbon from valerian essence, the name ''bornéène'', and, to camphor itself, that of ''borneol''.)</ref> Borneol can be found in several species of '']'',<ref>{{cite journal|last1=Lincoln |first1=D. E. |first2=B. M. |last2=Lawrence |date=1984 |title=The volatile constituents of camphorweed, ''Heterotheca subaxillaris'' |journal=Phytochemistry |volume=23 |issue=4 |page=933–934}}</ref> '']'', ''Rosmarinus officinalis'' (])<ref>{{cite journal |pmid=24584866|year=2013 |last1=Begum |first1=A. |last2=Sandhya |first2=S. |last3=Shaffath Ali |first3=S. |last4=Vinod |first4=K. R. |last5=Reddy |first5=S. |last6=Banji |first6=D. |title=An in-depth review on the medicinal flora ''Rosmarinus officinalis'' (Lamiaceae) |journal=Acta Scientiarum Polonorum: Technologia Alimentaria |volume=12 |issue=1 |pages=61–73 }}</ref><!--'']'',<ref>"Species Information". sun.ars-grin.gov. Retrieved 2008-03-02.</ref>--> '']'', '']'' and '']''.<ref name=ceor>{{cite journal | last1 = Wong | first1 = K. C. | last2 = Ong | first2 = K. S. | last3 = Lim | first3 = C. L. | title = Composition of the essential oil of rhizomes of ''Kaempferia galanga'' L. | journal = Flavour and Fragrance Journal | year = 2006 | volume = 7 | issue = 5 | pages = 263–266 | doi = 10.1002/ffj.2730070506 }}</ref> |
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It is one of the chemical compounds found in ]. This compound is gathered from the beaver's plant food.<ref>The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 ()</ref> |
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:] |
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===Synthesis=== |
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Borneol exists as two ]s which have two different ]. Naturally occurring d-(+)-borneol is ]. It can be found in several species of '']'', '']'', '']'' and '']''<ref name=ceor>{{cite journal |
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Borneol can be synthesized by ] of ] by the ] (a reversible process). Industrially, a racemic mixture of camphor is used, leading to a racemic mixture of borneol and ]. The chirality can be controlled by changing the chirality of camphor: (+)-camphor gives (−)-isoborneol and (+)-borneol.<ref>{{cite journal |last1=Yang |first1=Ming-Yeh |last2=Khine |first2=Aye Aye |last3=Liu |first3=Jen-Wei |last4=Cheng |first4=Hui-Chen |last5=Hu |first5=Anren |last6=Chen |first6=Hao-Ping |last7=Shih |first7=Tzenge-Lien |title=Resolution of isoborneol and its isomers by GC/MS to identify "synthetic" and "semi-synthetic" borneol products |journal=Chirality |date=November 2018 |volume=30 |issue=11 |pages=1233–1239 |doi=10.1002/chir.23017|pmid=30222211 }}</ref> |
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| last = Wong |
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| first = K. C. ''et al.'' |
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| authorlink = |
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| coauthors = |
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| title = Compositon of the essential oil of rhizomes of kaempferia galanga L. |
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| journal = Flavour and Fragrance Journal |
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| volume = 7 |
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| issue = 5 |
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| pages = 263–266 |
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| publisher = |
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| location = |
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| date = 2006 |
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| url = |
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| issn = |
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| doi = 10.1002/ffj.2730070506 |
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| id = |
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| accessdate = 2 July 2009 |
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| last2 = Ong |
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| first2 = K. S. |
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| last3 = Lim |
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| first3 = C. L.}}</ref> |
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. |
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Reduction of camphor with ] (fast and irreversible) gives instead the ] ]. |
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Borneol is used in ] as ]. An early description is found in the ]. |
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:] |
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Borneol is a component of many ]s,<ref> (Dr. Duke's Phytochemical and Ethnobotanical Databases)]</ref> and it is a natural ].<ref>{{cite web |url=http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL |title=Chemical Information |publisher=sun.ars-grin.gov |accessdate=2008-03-02}}</ref> |
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===Natural sources=== |
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==Use in organic chemistry== |
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Industrially, natural (+)-borneol is produced from '']'' (one specific chemotype)<ref>{{cite journal |last1=Li |first1=Fangping |last2=Huang |first2=Shilin |last3=Mei |first3=Yu |last4=Wu |first4=Bingqi |last5=Hou |first5=Zhuangwei |last6=Zhan |first6=Penglin |last7=Hou |first7=Zhihao |last8=Huang |first8=Wenjie |last9=Zhao |first9=Junliang |last10=Wang |first10=Jihua |title=Genome assembly provided new insights into the ''Cinnamomum burmannii'' evolution and <small>D</small>-borneol biosynthesis differences between chemotypes |journal=Industrial Crops and Products |date=October 2022 |volume=186 |pages=115181 |doi=10.1016/j.indcrop.2022.115181}}</ref> and '']''.<ref>{{cite journal |last1=Xingxing |first1=Liu |last2=Xi |first2=Zhang |last3=Xiali |first3=Guo |last4=Shangji |first4=Gong |last5=Xiangmei |first5=Jiang |last6=Yuxin |first6=Fu |last7=Liping |first7=Luo |title=Multivariate Analyses of Volatile Chemical Composition in Leaves of Different ''Cinnamomum camphora'' Chemotypes |journal=Chinese Bulletin of Botany |date=2014 |volume=49 |issue=2 |pages=161 |doi=10.3724/SP.J.1259.2014.00161}}</ref> |
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Derivatives of isoborneol are used as chiral ]s in ]: |
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* (2S)-(−)-3-exo-(morpholino)isoborneol or '''MIB'''<ref>Young K. Chen, Sang-Jin Jeon, Patrick J. Walsh, and William A. Nugent ], Vol. 82, p.87 (2005) </ref> with a ] ] in the α-hydroxyl position |
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* (2S)-(−)-3-exo-(dimethylamino)isoborneol or '''DAIB'''<ref>James D. White, Duncan J. Wardrop, and Kurt F. Sundermann ], Coll. Vol. 10, p.305 (2004); Vol. 79, p.130 (2002) .</ref> with a ] ] in the α-hydroxyl position |
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Natural (-)-borneol occurs in '']''. |
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==Isoborneol== |
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The related '''isoborneol''' is the ]. |
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===Biosynthesis=== |
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:] |
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Borneol is synthesized using ] as the starting material. DMAPP is then converted to ], which is acted upon by a ] to yield a bornyl diphosphate. A phosphatase then removes the phosphate groups, yielding borneol.<ref name=biosynminus>{{cite journal |last1=Ma |first1=Rui |last2=Su |first2=Ping |last3=Ma |first3=Qing |last4=Guo |first4=Juan |last5=Chen |first5=Suiqing |last6=Jin |first6=Baolong |last7=Zhang |first7=Haiyan |last8=Tang |first8=Jinfu |last9=Zhou |first9=Tao |last10=Xiao |first10=Chenghong |last11=Cui |first11=Guanghong |last12=Huang |first12=Luqi |title=Identification of (−)-bornyl diphosphate synthase from ''Blumea balsamifera'' and its application for (−)-borneol biosynthesis in ''Saccharomyces cerevisiae'' |journal=Synthetic and Systems Biotechnology |date=March 2022 |volume=7 |issue=1 |pages=490–497 |doi=10.1016/j.synbio.2021.12.004 |pmid=34977393 |pmc=8671873}}</ref> |
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The chirality of borneol in a plant depends on the preferred chirality of the bornyl diphosphate synthase. Synthases for either chirality have been sequenced.<ref name=biosynminus/><ref>{{cite journal |last1=Yang |first1=Zerui |last2=An |first2=Wenli |last3=Liu |first3=Shanshan |last4=Huang |first4=Yuying |last5=Xie |first5=Chunzhu |last6=Huang |first6=Song |last7=Zheng |first7=Xiasheng |title=Mining of candidate genes involved in the biosynthesis of dextrorotatory borneol in ''Cinnamomum burmannii'' by transcriptomic analysis on three chemotypes |journal=PeerJ |date=10 June 2020 |volume=8 |pages=e9311 |doi=10.7717/peerj.9311 |doi-access=free |pmid=32566406 |pmc=7293187}}</ref> |
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==Toxicology== |
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Borneol is an eye, skin, and respiratory irritant; and is harmful if swallowed.<ref></ref> |
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A downstream product is ] of either chirality, a reaction catalyzed by ] or ]. |
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==Notes and references== |
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{{Reflist}} |
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==External links== |
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== Uses == |
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Whereas ''d''-borneol was the ] that used to be the most readily available commercially, the more commercially available enantiomer now is ''l''-borneol, which also occurs in nature. |
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(+)-Borneol from '']'' spp. is used in ]. An early description is found in the ]. |
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Borneol is a component of many ]s<ref> {{webarchive|url=https://web.archive.org/web/20150923174038/http://www.ars-grin.gov/cgi-bin/duke/highchem.pl?chem=borneol&allchems=x |date=2015-09-23 }} (Dr. Duke's Phytochemical and Ethnobotanical Databases)]</ref> and it is a natural ].<ref>{{cite web|url=http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL |title=Chemical Information |publisher=sun.ars-grin.gov |access-date=2008-03-02 |url-status=dead |archive-url=https://web.archive.org/web/20041107161247/http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL |archive-date=2004-11-07 }}</ref> It also generates a ]-mediated cooling sensation similar to ].<ref>{{cite journal |last1=Chen |first1=GL |last2=Lei |first2=M |last3=Zhou |first3=LP |last4=Zeng |first4=B |last5=Zou |first5=F |title=Borneol Is a TRPM8 Agonist that Increases Ocular Surface Wetness |journal=PLOS One |date=2016 |volume=11 |issue=7 |pages=e0158868 |doi=10.1371/journal.pone.0158868 |pmid=27448228|pmc=4957794 |bibcode=2016PLoSO..1158868C |doi-access=free }}</ref> |
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Laevo-borneol is used in perfumery. It has a balsamic odour type with pine, woody and camphoraceous facets. |
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Dextro-borneol (dexborneol) is used in ], a drug approved in China for stroke.<ref>{{cite journal |last1=Xu |first1=Jie |last2=Wang |first2=Anxin |last3=Meng |first3=Xia |last4=Yalkun |first4=Gulbahram |last5=Xu |first5=Anding |last6=Gao |first6=Zhiqiang |last7=Chen |first7=Huisheng |last8=Ji |first8=Yong |last9=Xu |first9=Jun |last10=Geng |first10=Deqin |last11=Zhu |first11=Runxiu |last12=Liu |first12=Bo |last13=Dong |first13=Aiqin |last14=Mu |first14=Hua |last15=Lu |first15=Zhihong |last16=Li |first16=Shuya |last17=Zheng |first17=Huaguang |last18=Chen |first18=Xia |last19=Wang |first19=Yilong |last20=Zhao |first20=Xingquan |last21=Wang |first21=Yongjun |last22=Wang |first22=Yongjun |last23=Xu |first23=Anding |last24=Zhao |first24=Xingquan |last25=Chen |first25=Xia |last26=Wang |first26=Yongjun |last27=Meng |first27=Xia |last28=Wang |first28=Yilong |last29=Xu |first29=Jie |last30=Wang |first30=Anxin |last31=Zheng |first31=Huaguang |last32=Gao |first32=Zhiqiang |last33=Duan |first33=Lei |last34=Zhang |first34=Jinghua |last35=Li |first35=Shuya |last36=Lou |first36=Donghua |last37=Gao |first37=Zhiqiang |last38=Chen |first38=Huisheng |last39=Ji |first39=Yong |last40=Xu |first40=Jun |last41=Geng |first41=Deqin |last42=Zhu |first42=Runxiu |last43=Liu |first43=Bo |last44=Dong |first44=Aiqin |last45=Liang |first45=Qingcheng |last46=Yang |first46=Hong |last47=Guo |first47=Cunju |last48=Li |first48=Xin |last49=He |first49=Mingli |last50=Tian |first50=Xiangyang |last51=Cui |first51=Yong |last52=Zhou |first52=Junshan |last53=Wang |first53=Ning |last54=Wang |first54=Lei |last55=Zhang |first55=Xinjiang |last56=Gao |first56=Xiaoping |last57=Lu |first57=Liping |last58=Li |first58=Tong |last59=Cheng |first59=Yan |last60=Liu |first60=Kaixiang |last61=Xi |first61=Xiaokun |last62=Wang |first62=Baojun |last63=Sun |first63=Lin |last64=Zhao |first64=Shigang |last65=Chu |first65=Xiaofan |last66=Lian |first66=Yajun |last67=Yan |first67=Fuling |last68=Wang |first68=Xiaoshan |last69=Wang |first69=Dong |last70=Shao |first70=Bei |last71=Jiao |first71=Jinsong |last72=Wu |first72=Heng |last73=Li |first73=Guanglai |last74=Guo |first74=Libin |last75=Wang |first75=Yongjun |last76=Pan |first76=Suyue |last77=Xu |first77=Anding |last78=Li |first78=Heng |last79=Zhuang |first79=Jianhua |last80=Li |first80=Xin |last81=Wu |first81=Jun |last82=Wang |first82=Anxin |last83=Lou |first83=Donghua |last84=Zuo |first84=Yingting |last85=Zhang |first85=Yijun |last86=Zhang |first86=Xiaoli |last87=Feng |first87=Xiaofei |last88=Meng |first88=Xia |last89=Wang |first89=David |last90=Dong |first90=Kehui |last91=Liu |first91=Yanfang |last92=Li |first92=Hao |last93=Chen |first93=Dawei |last94=Lv |first94=Qiushi |title=Edaravone Dexborneol Versus Edaravone Alone for the Treatment of Acute Ischemic Stroke: A Phase III, Randomized, Double-Blind, Comparative Trial |journal=Stroke |date=March 2021 |volume=52 |issue=3 |pages=772–780 |doi=10.1161/STROKEAHA.120.031197|pmid=33588596 }}</ref> |
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== Toxicology == |
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Borneol may cause eye, skin, and respiratory irritation; it is harmful if swallowed.<ref>. ''Fisher Scientific''.</ref> Acute exposure may cause headache, nausea, vomiting, dizziness, lightheadedness, and syncope. Exposure to higher levels or over a longer period of time may cause restlessness, difficulty concentrating, irritability, and seizures.<ref name="HDS"> (PDF)</ref> |
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=== Skin irritation === |
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Borneol has been shown to have little to no irritation effect when applied to the human skin at doses used in fine fragrance formulation.<ref name=":0">{{Cite journal|last1=Bhatia|first1=S.P.|last2=Letizia|first2=C.S.|last3=Api|first3=A.M.|date=November 2008|title=Fragrance material review on borneol|url=https://linkinghub.elsevier.com/retrieve/pii/S0278691508003219|journal=Food and Chemical Toxicology|language=en|volume=46|issue=11|pages=S77–S80|doi=10.1016/j.fct.2008.06.031|pmid=18640181}}</ref> Skin exposure can lead to sensitization and a future ] even to small quantities.<ref name="HDS" /> |
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==Derivatives== |
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The bornyl group is a univalent radical C<sub>10</sub>H<sub>17</sub> derived from borneol by removal of hydroxyl and is also known as 2-bornyl.<ref>{{cite web|url=https://www.merriam-webster.com/dictionary/bornyl|title=Definition of BORNYL|website=www.merriam-webster.com}}</ref> Isobornyl is the univalent radical C<sub>10</sub>H<sub>17</sub> that is derived from isoborneol.<ref>{{cite web|url=https://www.merriam-webster.com/dictionary/isobornyl|title=Definition of ISOBORNYL|website=www.merriam-webster.com}}</ref> The ] ] is also a widely used compound derived from certain ]s. |
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] is the ] ] of borneol. |
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== Notes and references == |
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{{Reflist|2}} |
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== External links == |
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{{GABAAR PAMs}} |
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