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Borneol

Names
IUPAC name rel-(1R,2S,4R)-1,7,7-Trimethylbicycloheptan-2-ol
Other names 1,7,7-Trimethylbicycloheptan-2-endo-ol endo-2-Bornanol, Borneo camphor
Identifiers
CAS Number	507-70-0 (+/-)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15393
ChEMBL	ChEMBL486208
ChemSpider	5026296
ECHA InfoCard	100.006.685
EC Number	207-352-6
IUPHAR/BPS	6413
KEGG	C01411
PubChem CID	6552009
UNII	M89NIB437X
UN number	1312
CompTox Dashboard (EPA)	DTXSID2058700
InChI InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1Key: DTGKSKDOIYIVQL-WEDXCCLWSA-N InChI=1/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1Key: DTGKSKDOIYIVQL-WEDXCCLWBQ
SMILES O1C2CC1(C)C2(C)C
Properties
Chemical formula	C10H18O
Molar mass	154.253 g·mol
Appearance	colorless to white lumps
Odor	pungent, camphor-like
Density	1.011 g/cm (20 °C)
Melting point	208 °C (406 °F; 481 K)
Boiling point	213 °C (415 °F; 486 K)
Solubility in water	slightly soluble (D-form)
Solubility	soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin
Magnetic susceptibility (χ)	−1.26×10 cm/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H228
Precautionary statements	P210, P240, P241, P280, P370+P378
NFPA 704 (fire diamond)	2 2 0
Flash point	65 °C (149 °F; 338 K)
Safety data sheet (SDS)	External MSDS
Related compounds
Related compounds	Bornane (hydrocarbon)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. The exo diastereomer is called isoborneol. Being chiral, borneol exists as enantiomers, both of which are found in nature: d-borneol (also written (+)-borneol) and l-borneol ((-)-borneol).

Reactions

Borneol is oxidized to the ketone (camphor).

Occurrence

The compound was named in 1842 by the French chemist Charles Frédéric Gerhardt. Borneol can be found in several species of Heterotheca, Artemisia, Rosmarinus officinalis (rosemary) Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga.

It is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's plant food.

Synthesis

Borneol can be synthesized by reduction of camphor by the Meerwein–Ponndorf–Verley reduction (a reversible process). Industrially, a racemic mixture of camphor is used, leading to a racemic mixture of borneol and isoborneol. The chirality can be controlled by changing the chirality of camphor: (+)-camphor gives (−)-isoborneol and (+)-borneol.

Reduction of camphor with sodium borohydride (fast and irreversible) gives instead the diastereomer isoborneol.

Natural sources

Industrially, natural (+)-borneol is produced from Cinnamomum burmanni (one specific chemotype) and Cinnamomum camphora.

Natural (-)-borneol occurs in Blumea balsamifera.

Biosynthesis

Borneol is synthesized using DMAPP as the starting material. DMAPP is then converted to GPP, which is acted upon by a bornyl diphosphate synthase to yield a bornyl diphosphate. A phosphatase then removes the phosphate groups, yielding borneol.

The chirality of borneol in a plant depends on the preferred chirality of the bornyl diphosphate synthase. Synthases for either chirality have been sequenced.

A downstream product is camphor of either chirality, a reaction catalyzed by (+)-borneol dehydrogenase or (-)-borneol dehydrogenase.

Uses

Whereas d-borneol was the enantiomer that used to be the most readily available commercially, the more commercially available enantiomer now is l-borneol, which also occurs in nature.

(+)-Borneol from Dipterocarpus spp. is used in traditional Chinese medicine. An early description is found in the Bencao Gangmu.

Borneol is a component of many essential oils and it is a natural insect repellent. It also generates a TRPM8-mediated cooling sensation similar to menthol.

Laevo-borneol is used in perfumery. It has a balsamic odour type with pine, woody and camphoraceous facets.

Dextro-borneol (dexborneol) is used in edaravone/dexborneol, a drug approved in China for stroke.

Toxicology

Borneol may cause eye, skin, and respiratory irritation; it is harmful if swallowed. 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.

Skin irritation

Borneol has been shown to have little to no irritation effect when applied to the human skin at doses used in fine fragrance formulation. Skin exposure can lead to sensitization and a future allergic reaction even to small quantities.

Derivatives

The bornyl group is a univalent radical C₁₀H₁₇ derived from borneol by removal of hydroxyl and is also known as 2-bornyl. Isobornyl is the univalent radical C₁₀H₁₇ that is derived from isoborneol. The structural isomer fenchol is also a widely used compound derived from certain essential oils.

Bornyl acetate is the acetate ester of borneol.

Notes and references

1. Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton, Florida: CRC Press. p. 3.56. ISBN 0-8493-0486-5.
2. C. Gerhardt (1842) "Sur la transformation de l'essence de valériane en camphre de Bornéo et en camphre des laurinées" (On the transformation of the essence of valerian into Borneo camphor and into laurel camphor), Comptes rendus, 14 : 832-835. From p. 834: "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.)
3. Lincoln, D.E., B.M. Lawrence. 1984. "The volatile constituents of camphorweed, Heterotheca subaxillaris". Phytochemistry 23(4): 933-934
4. Begum, A.; Sandhya, S.; Shaffath Ali, S.; Vinod, K. R.; Reddy, S.; Banji, D. (2013). "An in-depth review on the medicinal flora Rosmarinus officinalis (Lamiaceae)". Acta Scientiarum Polonorum. Technologia Alimentaria. 12 (1): 61–73. PMID 24584866.
5. Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Composition of the essential oil of rhizomes of Kaempferia Galanga L.". Flavour and Fragrance Journal. 7 (5): 263–266. doi:10.1002/ffj.2730070506.
6. The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)
7. Yang, Ming-Yeh; Khine, Aye Aye; Liu, Jen-Wei; Cheng, Hui-Chen; Hu, Anren; Chen, Hao-Ping; Shih, Tzenge-Lien (November 2018). "Resolution of isoborneol and its isomers by GC/MS to identify "synthetic" and "semi-synthetic" borneol products". Chirality. 30 (11): 1233–1239. doi:10.1002/chir.23017. PMID 30222211.
8. Li, Fangping; Huang, Shilin; Mei, Yu; Wu, Bingqi; Hou, Zhuangwei; Zhan, Penglin; Hou, Zhihao; Huang, Wenjie; Zhao, Junliang; Wang, Jihua (October 2022). "Genome assembly provided new insights into the Cinnamomum burmannii evolution and D-borneol biosynthesis differences between chemotypes". Industrial Crops and Products. 186: 115181. doi:10.1016/j.indcrop.2022.115181.
9. Xingxing, Liu; Xi, Zhang; Xiali, Guo; Shangji, Gong; Xiangmei, Jiang; Yuxin, Fu; Liping, Luo (2014). "Multivariate Analyses of Volatile Chemical Composition in Leaves of Different Cinnamomum camphora Chemotypes". Chinese Bulletin of Botany. 49 (2): 161. doi:10.3724/SP.J.1259.2014.00161.
10. ^ Ma, Rui; Su, Ping; Ma, Qing; Guo, Juan; Chen, Suiqing; Jin, Baolong; Zhang, Haiyan; Tang, Jinfu; Zhou, Tao; Xiao, Chenghong; Cui, Guanghong; Huang, Luqi (March 2022). "Identification of (-)-bornyl diphosphate synthase from Blumea balsamifera and its application for (-)-borneol biosynthesis in Saccharomyces cerevisiae". Synthetic and Systems Biotechnology. 7 (1): 490–497. doi:10.1016/j.synbio.2021.12.004. PMC 8671873. PMID 34977393.
11. Yang, Zerui; An, Wenli; Liu, Shanshan; Huang, Yuying; Xie, Chunzhu; Huang, Song; Zheng, Xiasheng (10 June 2020). "Mining of candidate genes involved in the biosynthesis of dextrorotatory borneol in Cinnamomum burmannii by transcriptomic analysis on three chemotypes". PeerJ. 8: e9311. doi:10.7717/peerj.9311. PMC 7293187. PMID 32566406.
12. Plants containing borneol Archived 2015-09-23 at the Wayback Machine (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
13. "Chemical Information". sun.ars-grin.gov. Archived from the original on 2004-11-07. Retrieved 2008-03-02.
14. Chen, GL; Lei, M; Zhou, LP; Zeng, B; Zou, F (2016). "Borneol Is a TRPM8 Agonist that Increases Ocular Surface Wetness". PLOS ONE. 11 (7): e0158868. Bibcode:2016PLoSO..1158868C. doi:10.1371/journal.pone.0158868. PMC 4957794. PMID 27448228.
15. Xu, Jie; Wang, Anxin; Meng, Xia; Yalkun, Gulbahram; Xu, Anding; Gao, Zhiqiang; Chen, Huisheng; Ji, Yong; Xu, Jun; Geng, Deqin; Zhu, Runxiu; Liu, Bo; Dong, Aiqin; Mu, Hua; Lu, Zhihong; Li, Shuya; Zheng, Huaguang; Chen, Xia; Wang, Yilong; Zhao, Xingquan; Wang, Yongjun; Wang, Yongjun; Xu, Anding; Zhao, Xingquan; Chen, Xia; Wang, Yongjun; Meng, Xia; Wang, Yilong; Xu, Jie; Wang, Anxin; Zheng, Huaguang; Gao, Zhiqiang; Duan, Lei; Zhang, Jinghua; Li, Shuya; Lou, Donghua; Gao, Zhiqiang; Chen, Huisheng; Ji, Yong; Xu, Jun; Geng, Deqin; Zhu, Runxiu; Liu, Bo; Dong, Aiqin; Liang, Qingcheng; Yang, Hong; Guo, Cunju; Li, Xin; He, Mingli; Tian, Xiangyang; Cui, Yong; Zhou, Junshan; Wang, Ning; Wang, Lei; Zhang, Xinjiang; Gao, Xiaoping; Lu, Liping; Li, Tong; Cheng, Yan; Liu, Kaixiang; Xi, Xiaokun; Wang, Baojun; Sun, Lin; Zhao, Shigang; Chu, Xiaofan; Lian, Yajun; Yan, Fuling; Wang, Xiaoshan; Wang, Dong; Shao, Bei; Jiao, Jinsong; Wu, Heng; Li, Guanglai; Guo, Libin; Wang, Yongjun; Pan, Suyue; Xu, Anding; Li, Heng; Zhuang, Jianhua; Li, Xin; Wu, Jun; Wang, Anxin; Lou, Donghua; Zuo, Yingting; Zhang, Yijun; Zhang, Xiaoli; Feng, Xiaofei; Meng, Xia; Wang, David; Dong, Kehui; Liu, Yanfang; Li, Hao; Chen, Dawei; Lv, Qiushi (March 2021). "Edaravone Dexborneol Versus Edaravone Alone for the Treatment of Acute Ischemic Stroke: A Phase III, Randomized, Double-Blind, Comparative Trial". Stroke. 52 (3): 772–780. doi:10.1161/STROKEAHA.120.031197. PMID 33588596.
16. Material Safety Data Sheet. Fisher Scientific.
17. ^ HAZARDOUS SUBSTANCE FACT SHEET (PDF)
18. Bhatia, S.P.; Letizia, C.S.; Api, A.M. (November 2008). "Fragrance material review on borneol". Food and Chemical Toxicology. 46 (11): S77–S80. doi:10.1016/j.fct.2008.06.031. PMID 18640181.
19. "Definition of BORNYL". www.merriam-webster.com.
20. "Definition of ISOBORNYL". www.merriam-webster.com.

External links

• NIST datasheet including full spectroscopic data
• Borneol in Chinese medicine

• Secondary alcohols
• Monoterpenes
• GABAA receptor positive allosteric modulators
• Bicyclic compounds
• Cyclopentanes
• Substances discovered in the 19th century