CITRONELLYL ACETATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H22O2
Molecular Weight	198.3019
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(CCOC(C)=O)CCC=C(C)C

InChI

InChIKey=JOZKFWLRHCDGJA-UHFFFAOYSA-N

InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C12H22O2
Molecular Weight	198.3019
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23562495 | https://aroma-products.basf.com/products/citronellyl-acetate/ | https://www.ncbi.nlm.nih.gov/pubmed/2609972

Citronellyl acetate, a monoterpene product of the secondary metabolism of plants is suitable for all kinds of fruity-floral compounds and flavor compositions. Citronellyl acetate is present mainly in Eucalyptus citriodora, which possesses different biological activities, including fungicidal, larvicidal and bactericidal. As a component of volatile oils from Pelargonium graveoleus Citronellyl acetate exhibited marginal antitumor activities. In addition, some studies revealed, that Citronellyl acetate possessed antinociceptive properties on acute pain. This this is achieved by the involvement of PKC, PKA, TRPV1, TRPA1, TRPM8, and ASIC in Citronellyl acetate's antinociceptive mechanism.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute pain 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23562495	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A new double coupling system: synthesis of citronellyl acetate via transacetylation to citronellol from acetyl coenzyme A produced from glucose and free fatty acids.	2001 Aug	11577744
Anticonflict effects of rose oil and identification of its active constituents.	2002 Nov 22	12409148
Volatile chemicals identified in extracts from newly hybrid citrus, dekopon (Shiranuhi mandarin Suppl. J.).	2002 Sep 11	12207474
Volatile ester formation in roses. Identification of an acetyl-coenzyme A. Geraniol/Citronellol acetyltransferase in developing rose petals.	2003 Apr	12692346
Character impact odorants of Citrus Hallabong [(C. unshiu Marcov x C. sinensis Osbeck) x C. reticulata Blanco] cold-pressed peel oil.	2003 Apr 23	12696958
Sensory and instrumental evaluation of catnip (Nepeta cataria L.) aroma.	2003 Jun 18	12797753
Influence of the number of repellent-treated and untreated food or water containers on intake by the European starling.	2005 Aug	15951054
Characteristic odor components of kumquat (Fortunella japonica Swingle) peel oil.	2005 Mar 9	15740053
The essential oils from Zanthoxylum schinifolium pericarp induce apoptosis of HepG2 human hepatoma cells through increased production of reactive oxygen species.	2005 May	15863882
[Extraction and determination of volatile constituents in leaves of Eucalyptus citriodora].	2005 Nov	16498999
Enantioselective transacetylation of (R,S)-beta-citronellol by propanol rinsed immobilized Rhizomucor miehei lipase.	2007 Apr 18	17880741
Biochemical characterization of AtuD from Pseudomonas aeruginosa, the first member of a new subgroup of acyl-CoA dehydrogenases with specificity for citronellyl-CoA.	2008 Mar	18310025
TRP and ASIC channels mediate the antinociceptive effect of citronellyl acetate.	2013 May 25	23562495

Patents

Sample Use Guides

In Vivo Use Guide

male Swiss mice: Citronellyl acetate was administered intragastrically (25, 50, 75, 100 and 200 mg/kg), and the two higher doses caused antinociceptive effects in the acetic acid model; the highest dose reduced pain for 4h after it was administered (200 mg/kg).

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:57:10 UTC 2023` Edited by `admin` on `Fri Dec 15 15:57:10 UTC 2023`
Record UNII	IZ420RT3OY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CITRONELLYL ACETATE

Official Name

English

ACETIC ACID, CITRONELLYL ESTER

Common Name

English

NSC-4893

Code

English

FEMA NO. 2311

Code

English

CITRONELLYL ACETATE [INCI]

Common Name

English

6-OCTEN-1-OL, 3,7-DIMETHYL-, 1-ACETATE

Common Name

English

CITRONELLYL ACETATE [FHFI]

Common Name

English

3,7-DIMETHYL-6-OCTEN-1-YL ACETATE

Systematic Name

English

CITRONELLYL ACETATE, (±)-

Systematic Name

English

2-OCTEN-8-OL, 2,6-DIMETHYL-, ACETATE

Systematic Name

English

CITRONELLYL ACETATE [FCC]

Common Name

English

(±)-CITRONELLYL ACETATE

Systematic Name

English

Classification Tree Code System Code

JECFA EVALUATION

CITRONELLYL ACETATE