BORNYL ACETATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H20O2
Molecular Weight	196.286
Optical Activity	( + / - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC[C@](C)([C@@H](C1)OC(C)=O)C2(C)C

InChI

InChIKey=KGEKLUUHTZCSIP-HOSYDEDBSA-N

InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10+,12+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25545915 | https://www.ncbi.nlm.nih.gov/pubmed/27061538

Bornyl acetate is the main volatile constituent in numerous conifer oils and some Chinese traditional herbs, which has displayed an anti-inflammatory effect. In addition was shown, that this compound had therapeutic potentials for the osteoarthritis and may be developed as a preventive agent for lung inflammatory diseases. In combination with 5-fluorouracil, bornyl acetate possesses the anticancer activity by inducing apoptosis, DNA fragmentation as well as G2/M cell cycle arrest.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
regulation of cell cycle G2/M phase transition 2 Target ID: GO:1902749 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27061538	Blocker 537

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25545915	Primary	Basic research	Unknown Approved Use Unknown
Lung inflammatory diseases 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24120240	Preventing	Preclinical	Unknown Approved Use Unknown
Gastric cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27061538	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Foliar and cortex oleoresin variability of silver fir (Abies alba Mill.) in Albania.	2001 Jul-Aug	11531086
[Study on the chemical constituents of the volatile oil from Lysimachia trientaloides Hemsl].	2002 May	12541960
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India.	2003 Jun	14764241
Total synthesis of dumsin. 1. Retrosynthetic strategy and the elaboration of key intermediates from (--)-bornyl acetate.	2003 Sep 5	12946130
[Studies on the analgesic and anti-inflammatory effect of bornyl acetate in volatile oil from Amomum villosum].	2004 Jun	15524301
The effect of selected monoterpenoids on the cellular slime mold, Dictyostelium discoideum NC4.	2004 Jun	15303320
Antibacterial and antifungal effects of essential oils from coniferous trees.	2004 Jun	15187434
Essential oil of Valeriana officinalis L. cultivars and their antimicrobial activity as influenced by harvesting time under commercial organic cultivation.	2004 Jun 16	15186117
[Profile-effect on quality control of Houttuynia cordata injection].	2005 Dec	16496683
Composition, enantiomeric distribution, and antibacterial activity of the essential oil of Achillea ligustica All. from Corsica.	2006 Aug 23	16910724
Chemical composition and biological activities of essential oil from the leaves of Sesuvium portulacastrum.	2006 Jan 3	16243465
Variation in chemical composition and antibacterial activities of essential oils from two species of Houttuynia THUNB.	2006 Jul	16819207
Chemical composition and antimicrobial activity of the essential oil from Ambrosia trifida L.	2006 Jul 25	17971726
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.	2007 Feb 26	17324258
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.	2007 Jul-Aug	17913064
Composition and enantiomeric analysis of the essential oil of the fruits and the leaves of Pistacia vera from Greece.	2007 Jun 30	17876292
Analysis by gas chromatography-mass spectrometry of essential oil from seeds and aerial parts of Ferulago angulata (Schlecht.) Boiss gathered in Nevakoh and Shahoo, Zagross mountain, West of Iran.	2007 Mar 1	19069871
Essential oil composition and antioxidant activity of aerial parts of Grindelia robusta from Central Italy.	2007 Sep	17600634
Essential oil composition of Valeriana officinalis L. roots cultivated in Iran. Comparative analysis between supercritical CO2 extraction and hydrodistillation.	2008 Feb 8	18164718
GC/MS of terpenes in walnut-tree leaves after accelerated solvent extraction.	2008 Jan	18069704
Context effects on odor processing: an event-related potential study.	2008 Jul 15	18485742
The clinical pharmacology of intranasal l-methamphetamine.	2008 Jul 21	18644153
Activity of essential oils and individual components against acetyl- and butyrylcholinesterase.	2008 Jul-Aug	18810999
Chemical composition and antimicrobial activity of essential oil from cones of Pinus koraiensis.	2008 Mar	18388468
Separation and identification of volatile constituents in Artemisia argyi flowers by GC-MS with SPME and steam distillation.	2008 May-Jun	18492349
Synthesis, chiroptical properties, and their theoretical simulation of some highly rotating benzotricamphor derivatives.	2009	19725094
Antinociceptive effect and GC/MS analysis of Rosmarinus officinalis L. essential oil from its aerial parts.	2009 Apr	19184968
Acaricidal activities of major constituents of essential oil of Juniperus chinensis leaves against house dust and stored food mites.	2009 Aug	19722401
Rosmarinus officinalis L.: chemical modifications of the essential oil and evaluation of antioxidant and antimicrobial activity.	2009 Dec	20120107
Chemical composition of hydrodistilled essential oil of Artemisia incana (L.) Druce and antimicrobial activity against foodborne microorganisms.	2009 Dec	20020464
Analysis of essential oils from different organs of Scutellaria baicalensis.	2010 Aug	21213540
Essential oil composition of four endemic Ferulago species growing in Turkey.	2010 Dec	21299129
The chemical composition and antimicrobial activity of the leaf oil of Cupressus lusitanica from Monteverde, Costa Rica.	2010 Jan	21808533
Salvadora persica.	2010 Jul	22228963
[Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS].	2010 Jul	21137366
Investigation of the volatile fraction of rosemary infusion extracts.	2010 Jul-Sep	21179360
Genetics, phosphorus availability, and herbivore-derived induction as sources of phenotypic variation of leaf volatile terpenes in a pine species.	2010 Oct	20952630

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

It was shown, that bornyl acetate elevated the expression of IL-11 at both the mRNA and protein levels. Normal human chondrocytes were pretreated with or without bornyl acetate at the concentrations of 50 and 100 ug/mL for 24H, followed by incubated with IL-1b 10 ug/mL for another 24 H.

Name

Type

Language

BORNYL ACETATE

Official Name

English

BICYCLO(2.2.1)HEPTAN-2-OL, 1,7,7-TRIMETHYL-, 2-ACETATE, (1R,2S,4R)-REL-

Common Name

English

BORNYL ACETATE [USAN]

Common Name

English

NEOL ACETATE

Common Name

English

(±)-BORNYL ACETATE

Systematic Name

English

NSC-407158

Code

English

BORNYL ACETATE [INCI]

Common Name

English

BORNYL ACETATE [FHFI]

Common Name

English

FEMA NO. 2159

Code

English

BORNYL ACETATE [MART.]

Common Name

English

BORNYL ACETATE [MI]

Common Name

English

BORNYL ACETATE [FCC]

Common Name

English

BORNYLACETATE

Systematic Name

English

DL-BORNYL ACETATE

Common Name

English

BICYCLO(2.2.1)HEPTAN-2-OL, 1,7,7-TRIMETHYL-, ACETATE, ENDO-

Common Name

English

ENDO-BORNYL ACETATE

Common Name

English

BORNYL ACETATE (CONSTITUENT OF CHAMOMILE) [DSC]

Common Name

English

Bornyl acetate [WHO-DD]

Common Name

English

1,7,7-TRIMETHYLBICYCLO(2.2.1)HEPTAN-2-OL ACETATE

Systematic Name

English

BICYCLO(2.2.1)HEPTAN-2-OL, 1,7,7-TRIMETHYL-, ACETATE, (1R,2S,4R)-REL-

Common Name

English

(1R,2S,4R)-REL-1,7,7-TRIMETHYLBICYCLO(2.2.1)HEPTAN-2-OL 2-ACETATE

Common Name

English

ENDO-1,7,7-TRIMETHYLBICYCLO(2.2.1)HEPT-2-YL ACETATE

Common Name

English

BORNEOL ACETATE

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 172.515