Geranyl acetate

Relevant Data

Chemical name	Geranyl acetate
CAS number	105-87-3
COE number	201
JECFA number	58
Flavouring type	substances
FL No.	09.011
Mixture	No
Purity of the named substance at least 95% unless otherwise specified	At least 90%; secondary components 4-6% geraniol and 1-2% nerol
Reference body	JECFA

From webgate.ec.europa.eu

2D Structure
CID	1549026
IUPAC Name	[(2E)-3,7-dimethylocta-2,6-dienyl] acetate
InChI	InChI=1S/C12H20O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,8H,5,7,9H2,1-4H3/b11-8+
InChI Key	HIGQPQRQIQDZMP-DHZHZOJOSA-N
Canonical SMILES	CC(=CCCC(=CCOC(=O)C)C)C
Molecular Formula	C12H20O2
Wikipedia	geranyl acetate

From Pubchem

Property Name	Property Value
Molecular Weight	196.29
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	6
Complexity	233.0
CACTVS Substructure Key Fingerprint	A A A D c e B w M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A A A A A D A C g g A I C C A A A B A C I A i D S C A A A A A A g A A A A C A A A A A g A B A I A I Q A C E A A A g A A I I A I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area	26.3
Monoisotopic Mass	196.146
Exact Mass	196.146
XLogP3	None
XLogP3-AA	3.5
Compound Is Canonicalized	True
Formal Charge	0
Heavy Atom Count	14
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Isotope Atom Count	0
Covalently-Bonded Unit Count	1

From Pubchem

Model	Result	Probability
Absorption
Blood-Brain Barrier	BBB+	0.9398
Human Intestinal Absorption	HIA+	0.9937
Caco-2 Permeability	Caco2+	0.6681
P-glycoprotein Substrate	Non-substrate	0.6152
P-glycoprotein Inhibitor	Non-inhibitor	0.7702
P-glycoprotein Inhibitor	Inhibitor	0.5960
Renal Organic Cation Transporter	Non-inhibitor	0.8380
Distribution
Subcellular localization	Mitochondria	0.6095
Metabolism
CYP450 2C9 Substrate	Non-substrate	0.8589
CYP450 2D6 Substrate	Non-substrate	0.8748
CYP450 3A4 Substrate	Substrate	0.5118
CYP450 1A2 Inhibitor	Non-inhibitor	0.7663
CYP450 2C9 Inhibitor	Non-inhibitor	0.8935
CYP450 2D6 Inhibitor	Non-inhibitor	0.9361
CYP450 2C19 Inhibitor	Non-inhibitor	0.8874
CYP450 3A4 Inhibitor	Non-inhibitor	0.9647
CYP Inhibitory Promiscuity	Low CYP Inhibitory Promiscuity	0.7180
Excretion
Toxicity
Human Ether-a-go-go-Related Gene Inhibition	Weak inhibitor	0.8928
Human Ether-a-go-go-Related Gene Inhibition	Non-inhibitor	0.8911
AMES Toxicity	Non AMES toxic	0.9385
Carcinogens	Carcinogens	0.5219
Fish Toxicity	High FHMT	0.9733
Tetrahymena Pyriformis Toxicity	High TPT	0.9980
Honey Bee Toxicity	High HBT	0.8605
Biodegradation	Ready biodegradable	0.9558
Acute Oral Toxicity	III	0.5909
Carcinogenicity (Three-class)	Non-required	0.5291

From admetSAR

Model	Value	Unit
Absorption
Aqueous solubility	-3.6996	LogS
Caco-2 Permeability	1.2198	LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity	1.5219	LD50, mol/kg
Fish Toxicity	0.2099	pLC50, mg/L
Tetrahymena Pyriformis Toxicity	1.0920	pIGC50, ug/L

From admetSAR

Route of Exposure
Mechanism of Toxicity
Metabolism
Toxicity Values
Lethal Dose
Carcinogenicity (IARC Classification)	No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level
Health Effects
Treatment
Reference

From T3DB

Kingdom	Organic compounds
Superclass	Lipids and lipid-like molecules
Class	Fatty Acyls
Subclass	Fatty alcohol esters
Intermediate Tree Nodes	Not available
Direct Parent	Fatty alcohol esters
Alternative Parents	Carboxylic acid esters Acyclic monoterpenoids Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Carbonyl compounds
Molecular Framework	Aliphatic acyclic compounds
Substituents	Fatty alcohol ester - Monoterpenoid - Acyclic monoterpenoid - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
Description	This compound belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

From ClassyFire

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular Weight:: 49761.245 Da

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

From T3DB

Chemical Names:	3,7-DIMETHYL-2,6-OCTADIEN-1-YL ACETATE
CAS number:	105-87-3
COE number:	201
JECFA number:	58
FEMA number:	2509
Evaluation year:	1997
ADI:	0-0.5 mg/kg bw (1979)
Meeting:	49
Specs Code:	N
Comments:	No safety concern at current levels of intake when used as a flavouring agent. The 1979 group ADI of 0-0.5 mg/kg bw for citral, geranyl acetate, citronellol, linalool, and linalyl acetate, expressed as citral, was maintained at the fifty-first (TRS 891/90, 1998) and sixty-first (TRS for JECFA 61 in press) meetings.
Report:	TRS 884-JECFA 49/64
Tox Monograph:	FAS 40-JECFA 49/329
Specification:	COMPENDIUM ADDENDUM 9/FNP 52 Add.9/110 (2001)