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.
Laevo-borneol is used in perfumery. It has a balsamic odour type with pine, woody and camphoraceous facets.
Toxicology
Borneol may cause eye, skin, and respiratory irritation; it is harmful if swallowed.[10] 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.[11]
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.[12] Skin exposure can lead to sensitization and a future allergic reaction even to small quantities.[11]
Derivatives
The bornyl group is a univalent radical C10H17 derived from borneol by removal of hydroxyl and is also known as 2-bornyl.[13] Isobornyl is the univalent radical C10H17 that is derived from isoborneol.[14] The structural isomerfenchol is also a widely used compound derived from certain essential oils.
^Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. p. 3.56. ISBN0-8493-0486-5.
^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 [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.)
^Lincoln, D.E., B.M. Lawrence. 1984. "The volatile constituents of camphorweed, Heterotheca subaxillaris". Phytochemistry 23(4): 933-934
^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.
^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.
^The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)
^Plants containing borneol 2015-09-23 at the Wayback Machine (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
^. sun.ars-grin.gov. Archived from the original on 2004-11-07. Retrieved 2008-03-02.
^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. PMC4957794. PMID 27448228.
^"Definition of ISOBORNYL". www.merriam-webster.com.
External links
NIST datasheet including full spectroscopic data
Borneol in Chinese medicine
January 28, 2023
borneol, bicyclic, organic, compound, terpene, derivative, hydroxyl, group, this, compound, placed, endo, position, diastereomer, called, isoborneol, being, chiral, borneol, exists, enantiomers, both, which, found, nature, namesiupac, name, trimethylbicyclo, h. 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 Borneol NamesIUPAC name rel 1R 2S 4R 1 7 7 Trimethylbicyclo 2 2 1 heptan 2 olOther names 1 7 7 Trimethylbicyclo 2 2 1 heptan 2 endo olendo 2 Bornanol Borneo camphorIdentifiersCAS Number 507 70 0 Y3D model JSmol Interactive imageChEBI CHEBI 15393 YChEMBL ChEMBL486208 YChemSpider 5026296 YECHA InfoCard 100 006 685EC Number 207 352 6IUPHAR BPS 6413KEGG C01411 YPubChem CID 6552009UNII M89NIB437X YUN number 1312CompTox Dashboard EPA DTXSID2058700InChI 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 YKey DTGKSKDOIYIVQL WEDXCCLWSA N YInChI 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 WEDXCCLWBQSMILES O C H 1C C H 2CC C 1 C C2 C CPropertiesChemical formula C 10H 18OMolar mass 154 253 g mol 1Appearance colorless to white lumpsOdor pungent camphor likeDensity 1 011 g cm3 20 C 1 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 tetralinMagnetic susceptibility x 1 26 10 4 cm3 molHazardsGHS labelling PictogramsSignal word WarningHazard statements H228Precautionary statements P210 P240 P241 P280 P370 P378NFPA 704 fire diamond 220Flash point 65 C 149 F 338 K Safety data sheet SDS External MSDSRelated compoundsRelated compounds Bornane hydrocarbon Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Reactions 2 Occurrence 2 1 Synthesis 3 Uses 4 Toxicology 4 1 Skin Irritation 5 Derivatives 6 Notes and references 7 External linksReactions EditBorneol is oxidized to the ketone camphor Occurrence EditThe compound was named in 1842 by the French chemist Charles Frederic Gerhardt 2 Borneol can be found in several species of Heterotheca 3 Artemisia Rosmarinus officinalis rosemary 4 Dipterocarpaceae 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 Edit Borneol can be synthesized by reduction of camphor by the Meerwein Ponndorf Verley reduction a reversible process Reduction of camphor with sodium borohydride fast and irreversible gives instead the diastereomer isoborneol Uses EditWhereas 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 7 and it is a natural insect repellent 8 It also generates a TRPM8 mediated cooling sensation similar to menthol 9 Laevo borneol is used in perfumery It has a balsamic odour type with pine woody and camphoraceous facets Toxicology EditBorneol may cause eye skin and respiratory irritation it is harmful if swallowed 10 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 11 Skin Irritation Edit Borneol has been shown to have little to no irritation effect when applied to the human skin at doses used in fine fragrance formulation 12 Skin exposure can lead to sensitization and a future allergic reaction even to small quantities 11 Derivatives EditThe bornyl group is a univalent radical C10H17 derived from borneol by removal of hydroxyl and is also known as 2 bornyl 13 Isobornyl is the univalent radical C10H17 that is derived from isoborneol 14 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 Edit Lide D R ed 2005 CRC Handbook of Chemistry and Physics 86th ed Boca Raton FL CRC Press p 3 56 ISBN 0 8493 0486 5 C Gerhardt 1842 Sur la transformation de l essence de valeriane en camphre de Borneo et en camphre des laurinees 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 a l hydrogene carbone de l essence de valeriane le nom deborneene et au camphre lui meme celui deborneol 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 borneene and to camphor itself that of borneol Lincoln D E B M Lawrence 1984 The volatile constituents of camphorweed Heterotheca subaxillaris Phytochemistry 23 4 933 934 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 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 The Beaver Its Life and Impact Dietland Muller Schwarze 2003 page 43 book at google books Plants containing borneol Archived 2015 09 23 at the Wayback Machine Dr Duke s Phytochemical and Ethnobotanical Databases Chemical Information sun ars grin gov Archived from the original on 2004 11 07 Retrieved 2008 03 02 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 Material Safety Data Sheet Fisher Scientific a b HAZARDOUS SUBSTANCE FACT SHEET 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 Definition of BORNYL www merriam webster com Definition of ISOBORNYL www merriam webster com External links EditNIST datasheet including full spectroscopic data Borneol in Chinese medicine Retrieved from https en wikipedia org w index php title Borneol amp oldid 1128190264, wikipedia, wiki, book, books, library,
