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

Molecular Formula	C12H20O2
Molecular Weight	196.286
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
[Profile-effect on quality control of Houttuynia cordata injection].	2005 Dec	16496683
Chemical composition and antimicrobial activity of the essential oils of Chrysanthemum indicum.	2005 Jan 4	15588664
25 years of natural product R&D with New South Wales agriculture.	2005 Oct 31	18007515
Variation in chemical composition and antibacterial activities of essential oils from two species of Houttuynia THUNB.	2006 Jul	16819207
[Analysis of volatile constituents in leaves of three cypress species by gas chromatography/mass spectrometry].	2006 Mar	16830472
Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries.	2006 Oct	17127661
Chemical composition and antimicrobial activity of Chamaecyparis obtusa leaf essential oil.	2007 Feb	17161919
Simultaneous distillation-extraction of high-value volatile compounds from Cistus ladanifer L.	2007 Feb 19	17386635
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.	2007 Feb 26	17324258
Chemical composition and antimicrobial and antioxidant activities of the essential oil and methanol extract of Hippomarathrum microcarpum (Bieb.) from Turkey.	2007 Feb 7	17263496
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
Terpenoid compositions, and antioxidant and antimicrobial properties of the rhizome essential oils of different Hedychium species.	2008 Feb	18293443
Essential oil composition of Valeriana officinalis L. roots cultivated in Iran. Comparative analysis between supercritical CO2 extraction and hydrodistillation.	2008 Feb 8	18164718
Variability of the needle essential oils of Pinus peuce from different populations in Montenegro and Serbia.	2008 Jul	18649304
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
[Characterization of chemical components of essential oil from flowers of Chrysanthemum morifolium produced in Anhui province].	2008 Oct	19166008
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
Essential oil variability in natural populations of Picea omorika, a rare European conifer.	2009 Feb	19235161
Assessment of the allelopathic potential of Juniperus ashei on germination and growth of Bouteloua curtipendula.	2009 Jan	19153797
Identification and quantification of the volatile constituents in Cnidium monnieri using supercritical fluid extraction followed by GC-MS.	2009 Jan	19072900
Composition and seasonal variation of the essential oil from Abies sachalinensis from Hokkaido, Japan.	2009 Jun	19634334
Radical Scavenging Activity of the Essential Oil of Silver Fir (Abies alba).	2009 May	19430614
Supercritical fluid extraction of the volatile oil from Santolina chamaecyparissus.	2009 Sep	19705372
Antimicrobial activity and essential oil composition of a new T. argyrophyllum (C. Koch) Tvzel var. argyrophyllum chemotype.	2010	20484836
Analysis of essential oils from different organs of Scutellaria baicalensis.	2010 Aug	21213540
In vitro synergistic efficacy of combination of amphotericin B with Myrtus communis essential oil against clinical isolates of Candida albicans.	2010 Aug	20189786
Essential oil composition of four endemic Ferulago species growing in Turkey.	2010 Dec	21299129
Compositional variability in essential oil from different parts of Alpinia speciosa from India.	2010 Feb	20334144
The chemical composition and antimicrobial activity of the leaf oil of Cupressus lusitanica from Monteverde, Costa Rica.	2010 Jan	21808533
Misidentification of tansy, Tanacetum macrophyllum, as yarrow, Achillea grandifolia: a health risk or benefit?	2010 Jan	20184036
Salvadora persica.	2010 Jul	22228963
[Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS].	2010 Jul	21137366
A DFT analysis of thermal decomposition reactions important to natural products.	2010 Jul	20734926
Investigation of the volatile fraction of rosemary infusion extracts.	2010 Jul-Sep	21179360
The volatile constituents of Salvia leucantha.	2010 Jun	20614830
Effects of foliar fertilization and arbuscular mycorrhizal colonization on Salvia officinalis L. growth, antioxidant capacity, and essential oil composition.	2010 Mar 15	20355101
Chemical composition and antibacterial activity of essential oils of Lantana camara, Ageratum houstonianum and Eupatorium adenophorum.	2010 May	20645797
Relation between developmental stage, sensory properties, and volatile content of organically and conventionally grown pac choi (Brassica rapa var. Mei Qing Choi).	2010 May	20546419
Essential oil composition and antioxidant and antimicrobial properties of the aerial parts of Salvia eremophila Boiss. from Iran.	2010 May	20211675
Genetics, phosphorus availability, and herbivore-derived induction as sources of phenotypic variation of leaf volatile terpenes in a pine species.	2010 Oct	20952630
Volatile oil profiles of the aerial parts of Jordanian garland, Chrysanthemum coronarium.	2010 Oct	20818927
Essential oils, phenolics, and antioxidant activities of different parts of cumin (Cuminum cyminum L.).	2010 Oct 13	20809647

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:04:29 GMT 2023` Edited by `admin` on `Fri Dec 15 15:04:29 GMT 2023`
Record UNII	213431586X
Record Status	`Validated (UNII)`
Record Version

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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