Relevant Data

Food Additives Approved in the United States

Flavouring Substances Approved by European Union:

  • Linalyl acetate [show]

General Information

Synonyms: BERGAMOL, 3,7-DIMETHYLOCTA-1,6-DIEN-3-YL ACETATE, LICAREOL ACETATE, LINALOOL ACETATE
Chemical Names: 1,5-DIMETHYL-1-ETHENYLHEX-4-ENYL ACETATE
CAS number: 115-95-7
COE number: 203
JECFA number: 359
FEMA number: 2636
Functional Class: Flavouring Agent
FLAVOURING_AGENT

From apps.who.int


Evaluations

Evaluation year: 1998
ADI: 0-0.5 mg/kg bw (1979)
Meeting: 23
Specs Code: R (1982)
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 891-JECFA 51/79
Tox Monograph: FAS 42-JECFA 51/293
Specification: COMPENDIUM ADDENDUM 6/FNP 52 Add.6/180 (1998)

From apps.who.int


Computed Descriptors

Download SDF
2D Structure
CID8294
IUPAC Name3,7-dimethylocta-1,6-dien-3-yl acetate
InChIInChI=1S/C12H20O2/c1-6-12(5,14-11(4)13)9-7-8-10(2)3/h6,8H,1,7,9H2,2-5H3
InChI KeyUWKAYLJWKGQEPM-UHFFFAOYSA-N
Canonical SMILESCC(=CCCC(C)(C=C)OC(=O)C)C
Molecular FormulaC12H20O2
Wikipedialinalyl acetate

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight196.29
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Complexity237.0
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 E S A g A A C C A A A B A C I A i D S C A A A A A A g A A A I C A A A A A g A B A I A I Q A C A A A E g A A I I A I A A A A 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 = =
Topological Polar Surface Area26.3
Monoisotopic Mass196.146
Exact Mass196.146
XLogP3None
XLogP3-AA3.3
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem


ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9701
Human Intestinal AbsorptionHIA+0.9738
Caco-2 PermeabilityCaco2+0.6908
P-glycoprotein SubstrateNon-substrate0.5851
P-glycoprotein InhibitorInhibitor0.5000
Non-inhibitor0.6249
Renal Organic Cation TransporterNon-inhibitor0.8737
Distribution
Subcellular localizationMitochondria0.5406
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8744
CYP450 2D6 SubstrateNon-substrate0.8970
CYP450 3A4 SubstrateSubstrate0.6263
CYP450 1A2 InhibitorNon-inhibitor0.6937
CYP450 2C9 InhibitorNon-inhibitor0.8555
CYP450 2D6 InhibitorNon-inhibitor0.9292
CYP450 2C19 InhibitorNon-inhibitor0.7144
CYP450 3A4 InhibitorNon-inhibitor0.8246
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7763
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9416
Non-inhibitor0.9231
AMES ToxicityNon AMES toxic0.9524
CarcinogensCarcinogens 0.5787
Fish ToxicityHigh FHMT0.8593
Tetrahymena Pyriformis ToxicityHigh TPT0.8999
Honey Bee ToxicityHigh HBT0.8847
BiodegradationReady biodegradable0.8414
Acute Oral ToxicityIV0.6409
Carcinogenicity (Three-class)Warning0.4855

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-3.0506LogS
Caco-2 Permeability1.3291LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.4627LD50, mol/kg
Fish Toxicity1.0987pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0540pIGC50, ug/L

From admetSAR


Toxicity Profile

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


Taxonomic Classification

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassMonoterpenoids
Intermediate Tree NodesNot available
Direct ParentAcyclic monoterpenoids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsAcyclic 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
DescriptionThis compound belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

From ClassyFire


Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. 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