Borneol

Borneol
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
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 ;
	show InChI
	show SMILES
Properties
Chemical formula	C10H18O
Molar mass	154.253 g·mol−1
Appearance	colorless to white lumps
Odor	pungent, camphor-like
Density	1.011 g/cm3 (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)	−1.26×10−4 cm3/mol
Hazards
Safety data sheet	External MSDS
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H228
GHS precautionary statements	P210, P240, P241, P280, P370+378
NFPA 704 (fire diamond)	2 2 0
Flash point	65 °C (149 °F; 338 K)
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).
	(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. Being chiral, borneol exists as two enantiomers. Both (+)-borneol (older name d-borneol) and (−)-borneol (l-borneol) are found in nature.

Reactions[]

Borneol is easily oxidized to the ketone (camphor). One historical name for borneol is Borneo camphor which explains the name.

Occurrence[]

The compound was named in 1842 by the French chemist Charles Frédéric Gerhardt.^[2] Borneol can be found in several species of Heterotheca,^[3] Artemisia, Callicarpa,^[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[]

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 isomer isoborneol as the kinetically controlled reaction product.

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^[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 as an aroma chemical in perfumery. It has a balsamic odour type with pine, woody and camphoraceous facets.

Use in organic chemistry[]

Derivatives of isoborneol are used as ligands in asymmetric synthesis:

(2S)-(−)-3-exo-(morpholino)isoborneol or MIB^[10] with a morpholine substituent in the α-hydroxyl position.
(2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB^[11] with a dimethylamino substituent in the α-hydroxyl position

Toxicology[]

Borneol may cause eye, skin, and respiratory irritation; it is harmful if swallowed.^[12]

Skin Irritation[]

Borneol has been shown to have little to no irritation effect when applied to the human skin at a small dose.^[13] However, a long term exposure to borneol may cause mild irritation.^[14]

Phototoxicity and photoallergy[]

Since Borneol does not absorb UV light at 290 nm to 400 nm, it doesn't have any phototoxic or photoallergic potential.^[13]

Derivatives[]

The bornyl group is a univalent radical C₁₀H₁₇ derived from borneol by removal of hydroxyl and is also known as 2-bornyl.^[15] Isobornyl is the univalent radical C₁₀H₁₇ that is derived from isoborneol.^[16] 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[]

^ 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 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
^ "Species Information". sun.ars-grin.gov. Retrieved 2008-03-02.
^ 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.
^ "(2S)-(−)-3-exo-(MORPHOLINO)ISOBORNEOL [(−)-MIB]". Organic Syntheses. 82: 87. 2005. doi:10.15227/orgsyn.082.0087.
^ "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]". Organic Syntheses. 79: 130. 2002. doi:10.15227/orgsyn.079.0130.
^ Material Safety Data Sheet, Fisher Scientific
^ Jump up to: ^a ^b 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.
^ HAZARDOUS SUBSTANCE FACT SHEET
^ "Definition of BORNYL". www.merriam-webster.com.
^ "Definition of ISOBORNYL". www.merriam-webster.com.

External links[]

[CRC-1] 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.

[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 [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] Lincoln, D.E., B.M. Lawrence. 1984. "The volatile constituents of camphorweed, Heterotheca subaxillaris". Phytochemistry 23(4): 933-934

[4] "Species Information". sun.ars-grin.gov. Retrieved 2008-03-02.

[ceor-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] Plants containing borneol Archived 2015-09-23 at the Wayback Machine (Dr. Duke's Phytochemical and Ethnobotanical Databases)]

[8] "Chemical Information". sun.ars-grin.gov. Archived from the original on 2004-11-07. Retrieved 2008-03-02.

[9] 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.

[10] "(2S)-(−)-3-exo-(MORPHOLINO)ISOBORNEOL [(−)-MIB]". Organic Syntheses. 82: 87. 2005. doi:10.15227/orgsyn.082.0087.

[11] "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]". Organic Syntheses. 79: 130. 2002. doi:10.15227/orgsyn.079.0130.

[12] Material Safety Data Sheet, Fisher Scientific

[:0-13] Jump up to: ^a ^b 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.

[14] HAZARDOUS SUBSTANCE FACT SHEET

[15] "Definition of BORNYL". www.merriam-webster.com.

[16] "Definition of ISOBORNYL". www.merriam-webster.com.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]

show v t GABA_A receptor positive modulators
Alcohols	Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol
Barbiturates	Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital
Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam
Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate
Flavonoids	Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Luteolin Skullcap constituents (e.g., baicalin) Wogonin
Imidazoles	Etomidate Metomidate Propoxate
Kava constituents	Desmethoxyyangonin Kavain Methysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Pregnanolone (eltanolone) Progesterone Renanolone Testosterone THDOC Zuranolone
Nonbenzodiazepines	Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684
Phenols	Fospropofol Propofol Thymol
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether
Others/unsorted	3-Hydroxybutanal Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, , dihydroergotamine, ergoloid (dihydroergotoxine)) Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Niacinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, ) Unsorted benzodiazepine site positive modulators: α-Pinene
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators