Borneol

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Borneol
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Names
IUPAC name
rel-(1R,2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
Other names
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-endo-ol
endo-2-Bornanol, Borneo camphor
Identifiers
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3D model (JSmol)
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UN number 1312
  • 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/s1 checkY
    Key: DTGKSKDOIYIVQL-WEDXCCLWSA-N checkY
  • (+/-): 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+/s2
    Key: DTGKSKDOIYIVQL-IUNFSSIHNA-N
  • O[C@H]1C[C@H]2CC[C@]1(C)C2(C)C
Properties
C10H18O
Molar mass 154.253 g·mol−1
Appearance colorless to white lumps
Odor pungent, camphor-like
Density 1.011 g/cm3 (20 °C)[1]
Melting point 208 °C (406 °F; 481 K)
Boiling point 213 °C (415 °F; 486 K)
slightly soluble (D-form)
Solubility soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin
−1.26×10−4 cm3/mol
Hazards
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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 [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

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, dextroborneol, dexborneol) and l-borneol (or (−)-borneol, levoborneol).

Both borneol and isoborneol belong to the category of 2-bornanol, a derivative of bornane. Some sources such as PubChem and CHEBI use the term borneol to refer to the entire category of 2-bornanols while others such as KEGG use the term borneol to refer to the compounds with endo hydroxyl only.

Reactions

Borneol is oxidized to the ketone camphor.

Occurrence

The compound was identified and named camphre de Bornéo, or Borneo camphor in 1842 by the French chemist Charles Frédéric Gerhardt.[2] Borneol can be found in several species of Heterotheca,[3] Artemisia, Rosmarinus officinalis (rosemary),[4] Dryobalanops aromatica, Blumea balsamifera and Kaempferia galanga.[5]

It is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's plant food.[6]

Synthesis

Borneol can be synthesized by reduction of camphor by the Meerwein–Ponndorf–Verley reduction (a reversible process). For flavoring purposes, a racemic mixture of camphor is used as starting material, 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.[7]

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

Synthesis of the borneol isomer isoborneol via reduction of camphor.

Natural sources

Borneol is a component of many essential oils.[8]

Industrially, natural (+)-borneol is produced from Cinnamomum burmanni (one specific chemotype)[9] and Cinnamomum camphora.[10][11]

Natural (-)-borneol occurs in Blumea balsamifera.[11]

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.[12]

The chirality of borneol in a plant depends on the preferred chirality of the bornyl diphosphate synthase. Synthases for either chirality have been sequenced.[12][13]

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

Uses

As mentioned above, both enantiomers of borneol occur in nature. Whereas d-borneol (+) was the enantiomer that used to be the most readily available commercially, the more commercially available enantiomer now is l-borneol (-).

Borneol generates a TRPM8-mediated cooling sensation similar to, but weaker than, menthol. It is more effective at activating TRPM8 at lower temperatures.[14]

Borneol is also a natural insect repellent.[15]

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

Medical uses

Dextro-borneol (dexborneol) is used in edaravone/dexborneol, a drug approved in China for stroke. It is approved in intravenous (2021) and sublingual (2025) forms. The intravenous combination was approved on the basis of trials showing it to be superior to edavarone alone.[16][17]

Folk medicine

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

Volume 1 of the modern Chinese Pharmacopoeia, which deals with TCM and modernized TCM, lists uses for both enantiomers as well as the synthetic racemer.[11]

Borneol is widely used in ophthalmic preparations in China, though little is known about its exact function.[14]

Toxicology

Borneol may cause eye, skin, and respiratory irritation; it is harmful if swallowed.[18] 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.[19]

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.[20] Skin exposure can lead to sensitization and a future allergic reaction even to small quantities.[19]

Derivatives

The bornyl group is a univalent radical C10H17 derived from borneol by removal of hydroxyl and is also known as 2-bornyl.[21] Isobornyl is the univalent radical C10H17 that is derived from isoborneol.[22] Bornyl acetate is the acetate ester of borneol.

The norborneols are derived from borneol and isoborneol by the removal of methyl groups, analogous to the change from bornane to norbornane.

The epiborneols and isoepiborneols are analogously derived from epicamphor.[23]

The structural isomer fenchol is a widely used compound derived from certain essential oils.

Notes and references

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  1. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.Gerhardt, C. (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 [namely, that the compound that Gerhardt had obtained from valerian oil was identical to that obtained by Pelouze from camphor from Borneo], to the hydrocarbon from valerian essence, the name bornéène, and, to camphor itself, that of borneol.)
  3. ^ Page Module:Citation/CS1/styles.css has no content.Lincoln, D. E.; Lawrence, B. M. (1984). "The volatile constituents of camphorweed, Heterotheca subaxillaris". Phytochemistry. 23 (4): 933–934. Bibcode:1984PChem..23..933L. doi:10.1016/S0031-9422(00)85073-6.
  4. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Plants containing borneol Script error: No such module "webarchive". (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
  9. ^ Page Module:Citation/CS1/styles.css has no content.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.
  10. ^ Page Module:Citation/CS1/styles.css has no content.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.
  11. ^ a b c Page Module:Citation/CS1/styles.css has no content.中国药典第一部 [Pharmacopoeia of the People's Republic of China, Volume 1] (2020 ed.). 右旋 (+) Script error: No such module "webarchive". 左旋 (-) Script error: No such module "webarchive". 合成 (racemic synthetic) Script error: No such module "webarchive".
  12. ^ a b Page Module:Citation/CS1/styles.css has no content.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.
  13. ^ Page Module:Citation/CS1/styles.css has no content.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.
  14. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."Chemical Information". sun.ars-grin.gov. Archived from the original on 2004-11-07. Retrieved 2008-03-02.
  16. ^ Page Module:Citation/CS1/styles.css has no content.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.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Fu, Yu; Wang, Anxin; Tang, Renhong; Li, Shuya; Tian, Xue; Xia, Xue; Ren, Jinsheng; Yang, Shibao; Chen, Rong; Zhu, Shunwei; Feng, Xiaofei; Yao, Jinliang; Wei, Yan; Dong, Xueshuang; Ling, Yun; Yi, Fei; Deng, Qian; Guo, Cunju; Sui, Yi; Han, Shugen; Wen, Guoqiang; Li, Chuanling; Dong, Aiqin; Sun, Xin; Wang, Zhimin; Shi, Xueying; Liu, Bo; Fan, Dongsheng (1 April 2024). "Sublingual Edaravone Dexborneol for the Treatment of Acute Ischemic Stroke: The TASTE-SL Randomized Clinical Trial". JAMA Neurology. 81 (4): 319. doi:10.1001/jamaneurol.2023.5716. PMC 10877503. PMID 38372981.
  18. ^ Material Safety Data Sheet. Fisher Scientific.
  19. ^ a b HAZARDOUS SUBSTANCE FACT SHEET (PDF)
  20. ^ Page Module:Citation/CS1/styles.css has no content.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.
  21. ^ Page Module:Citation/CS1/styles.css has no content."Definition of BORNYL". www.merriam-webster.com.
  22. ^ Page Module:Citation/CS1/styles.css has no content."Definition of ISOBORNYL". www.merriam-webster.com.
  23. ^ Page Module:Citation/CS1/styles.css has no content.Robertson, JS; Hussain, M (June 1969). "Metabolism of camphors and related compounds". The Biochemical Journal. 113 (1): 57–65. doi:10.1042/bj1130057. PMC 1184604. PMID 4308838.

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