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Details

Stereochemistry RACEMIC
Molecular Formula C10H18O
Molecular Weight 154.2497
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BORNEOL

SMILES

CC1(C)[C@]2([H])CC[C@@]1(C)[C@]([H])(C2)O

InChI

InChIKey=DTGKSKDOIYIVQL-WEDXCCLWSA-N
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

HIDE SMILES / InChI

Molecular Formula C10H18O
Molecular Weight 154.2497
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Borneol, a monoterpenoid alcohol, is a component of many essential oils. Barneol occurs in nature as a single enantiomer (d- or l-, depending on the oil type) or, less frequently, as the racemate. Several studies have proved the effectiveness of borneol. In Chinese medicines borneol has been used in relieving symptoms of anxiety, fatigue and insomnia; inducing anesthesia and analgesia to alleviate abdominal pain, wounds and burns; relieving rheumatic pain, hemorrhoids, skin diseases and ulcerations of the mouth, ears, eyes or nose; to treat sore throats and skin infections, and is mainly used to treat cardiovascular and cerebrovascular diseases. Borneol has a significant therapeutic effect on neuralgia. This compound is considered a GRAS approved by the FDA as food flavor. Additionally, borneol is a fragrance ingredient. GABAA, TRPV3, TRPM8 and TRPA1 have been identified as the molecular targets of borneol.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q7Z2W7
Gene ID: 79054.0
Gene Symbol: TRPM8
Target Organism: Homo sapiens (Human)
65.0 µM [EC50]
248.0 µM [EC50]
Target ID: Q8NET8
Gene ID: 162514.0
Gene Symbol: TRPV3
Target Organism: Homo sapiens (Human)
3.45 mM [EC50]
Target ID: O75762
Gene ID: 8989.0
Gene Symbol: TRPA1
Target Organism: Homo sapiens (Human)
0.2 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol.
2001 Sep
Chiral recognition of terpenoids in some pharmaceuticals derived from natural sources.
2002 Dec 31
Incorporation of [1-(13)C]1-deoxy-D-xylulose into isoprenoids of the liverwort Conocephalum conicum.
2002 Feb
Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi.
2003 Dec
Erythema multiforme due to contact with weeds: a recurrence after patch testing.
2003 Jan
Mechanistic studies on the bioactivation of diclofenac: identification of diclofenac-S-acyl-glutathione in vitro in incubations with rat and human hepatocytes.
2003 Nov
Essential oils from Mediterranean lamiaceae as weed germination inhibitors.
2003 Oct 8
The effect of applying a pipe-joint lubricant to connect ductile iron pipe on off-flavors in drinking water distribution systems.
2004
Thermodynamics of the molecular and chiral recognition of cycloalkanols and camphor by modified beta-cyclodextrins possessing simple aromatic tethers.
2004 Jan 9
Simultaneous expression of guinea pig UDP-glucuronosyltransferase 2B21 (UGT2B21) and 2B22 in COS-7 cells enhances UGT2B21-catalyzed chloramphenicol glucuronidation.
2004 Oct
Skeleton-selective fluorescent chemosensor based on cyclodextrin bearing a 4-amino-7-nitrobenz-2-oxa-1,3-diazole moiety.
2005 Dec 7
Chemical composition and antimicrobial activity of the essential oil of Artemisia lavandulaefolia.
2005 Jun
[The creation of laosun yutie plaster and safety experiment].
2005 May
Enantiomeric excess determination by fourier transform near-infrared vibrational circular dichroism spectroscopy: simulation of real-time process monitoring.
2005 Sep
[Effect of ligustrazine, synthetic borneol on lasting time of ciliary movement].
2006 Aug
Promoting effect of borneol on the permeability of puerarin eye drops and timolol maleate eye drops through the cornea in vitro.
2006 Sep
Chemical composition and antibacterial activities of the essential oil from Abies koreana.
2007 Dec
Cross-attraction between an exotic and a native pine bark beetle: a novel invasion mechanism?
2007 Dec 12
Composition of the essential oil of Salvia officinalis L. from various European countries.
2007 May
Absorptive profile of chlorogenic acid in rats.
2007 Sep
Percutaneous permeation enhancement by terpenes: mechanistic view.
2008
Antifungal, phytotoxic and insecticidal properties of essential oil isolated from Turkish Origanum acutidens and its three components, carvacrol, thymol and p-cymene.
2008 Dec
Tunisian Salvia officinalis L. and Schinus molle L. essential oils: their chemical compositions and their preservative effects against Salmonella inoculated in minced beef meat.
2008 Jul 31
[Characterization of chemical components of essential oil from cupitulum of Chrysanthemum morifolium cultivated in Tongxiang city].
2008 Mar
ThermoTRP channels in nociceptors: taking a lead from capsaicin receptor TRPV1.
2008 Mar
[Characterization of chemical components of essential oil from flowers of Chrysanthemum morifolium produced in Anhui province].
2008 Oct
Antimicrobial activity of the essential oil obtained from roots and chemical composition of the volatile constituents from the roots, stems, and leaves of Ballota nigra from Serbia.
2009 Apr
Phytotoxicity of constituents of glandular trichomes and the leaf surface of camphorweed, Heterotheca subaxillaris.
2009 Jan
[Determination of d-borneol in the different parts of Cinnamomum camphora by GC-MS].
2009 Jul
[Oral absorption enhancers of Ophiopogon japonicas polysaccharides].
2009 Jun
[Effects of borneol on pharmacokinetics of protocatechuic acid in rabbits].
2009 May
Application of headspace solid phase microextraction for study of noncovalent interaction of borneol with human serum albumin.
2009 Nov
Investigation of the volatile fraction of rosemary infusion extracts.
2010 Jul-Sep
Hepatoprotective potential of Decalepis hamiltonii (Wight and Arn) against carbon tetrachloride-induced hepatic damage in rats.
2010 Oct
Patents

Sample Use Guides

25 % borneol (d-form) was applied topically as a single dose for 30-60 min.
Route of Administration: Topical
Peripheral sensory neurons were treated with 200 uM (~0.003%) borneol (d-form). The drug increased the Ca2+ signal in a subset of dorsal root ganglion neurons.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:58:04 UTC 2021
Edited
by admin
on Sat Jun 26 13:58:04 UTC 2021
Record UNII
M89NIB437X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BORNEOL
FCC   FHFI   HSDB   INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
ENDO-BORNEOL
Common Name English
BORNEOL [MART.]
Common Name English
BORNEOL [FCC]
Common Name English
BORNEOL [FHFI]
Common Name English
BORNEOL, (+/-)-
Systematic Name English
BORNEOL, DL-
Common Name English
BINGPIAN
Common Name English
BORNEOL [INCI]
Common Name English
2-BORNEOL
Common Name English
NSC-60223
Code English
BORNEOL [HSDB]
Common Name English
REL-(1S,2R,4S)-1,7,7-TRIMETHYLBICYCLO(2.2.1)HEPTAN-2-OL
Common Name English
FEMA NO. 2157
Code English
BORNEOLUM SYNTHETICUM
CHP  
Common Name English
BORNEOL [MI]
Common Name English
HECHENGLONGNAO
Common Name English
CAMPHOL
Common Name English
BORNEOL [WHO-DD]
Common Name English
BICYCLO(2.2.1)HEPTAN-2-OL, 1,7,7-TRIMETHYL-, ENDO-
Common Name English
BORNEOL (CONSTITUENT OF BLACK PEPPER) [DSC]
Common Name English
BORNEOLUM SYNTHETICUM [CHP]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION BORNEOL
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
FDA ORPHAN DRUG 754420
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
Code System Code Type Description
MERCK INDEX
M2610
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY Merck Index
FDA UNII
M89NIB437X
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
WIKIPEDIA
BORNEOL
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
HSDB
946
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
CAS
507-70-0
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
MESH
C022871
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
RXCUI
1368202
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB11288
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
EVMPD
SUB13113MIG
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
EPA CompTox
507-70-0
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-080-0
Created by admin on Sat Jun 26 13:58:04 UTC 2021 , Edited by admin on Sat Jun 26 13:58:04 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Monoterpene Class
PARENT -> CONSTITUENT ALWAYS PRESENT
USP-DSC
Related Record Type Details
ACTIVE MOIETY