Structure Database (LMSD)

Common Name
Geranyl acetate
Systematic Name
3,7-Dimethyl-2E,6-octadienyl acetate
Synonyms
LM ID
LMFA07010189
Formula
Exact Mass
Calculate m/z
196.14633
Sum Composition
Status
Curated



Classification

Biological Context

Geranyl acetate is a monoterpene that has been found in C. sativa with diverse biological activities.1 It reduces compound action potential (CAP) peak amplitude in isolated frog sciatic nerves (IC50 = 0.51 mM).2 Geranyl acetate inhibits the radial growth of M. gypsum, T. vercossum, and C. tropicalis on solid media.3 It is sporicidal against B. subtilis when used at a concentration of 1% in an agar diffusion assay.4 Geranyl acetate inhibits growth of COLO 205 cells (IC50 = 30 μM) via induction of DNA damage, cell cycle arrest at the G2/M phase, and mitochondrial apoptosis.5

This information has been provided by Cayman Chemical

References

1. Fischedick, J.T. Identification of terpenoid chemotypes among high (–)-trans-Δ9-tetrahydrocannabinol-producing Cannabis sativa L. cultivars. Cannabis Cannabinoid Res. 2(1), 34-47 (2017).
3. Khayyat, S.A., and Sameeh, M.Y. Bioactive epoxides and hydroperoxides derived from naturally monoterpene geranyl acetate. Saudi Pharm. J. 26(1), 14-19 (2018).

References

Comments
Pherobase

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Magnoliopsida (#3398)
Pollen and flower volatiles in two Rosa species,
Phytochemistry, 1987

String Representations

InChiKey (Click to copy)
HIGQPQRQIQDZMP-DHZHZOJOSA-N
InChi (Click to copy)
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+
SMILES (Click to copy)
O(C(=O)C)C/C=C(\C)/CC/C=C(\C)/C

Other Databases

KEGG ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

Calculated Physicochemical Properties

Heavy Atoms 14
Rings 0
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 225.82
Topological Polar Surface Area 26.30
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2
logP 3.53
Molar Refractivity 59.55

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Created at
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Updated at
19th Jun 2024