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W412101

Sigma-Aldrich

Geranic acid

85%, stabilised

Synonym(s):

3,7-Dimethyl-2,6-octadienoic acid

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)=CHCO2H
CAS Number:
Molecular Weight:
168.23
FEMA Number:
4121
Beilstein/REAXYS Number:
1763804
EC Number:
MDL number:
UNSPSC Code:
12164502
PubChem Substance ID:
Flavis number:
8.081
NACRES:
NA.21

biological source

synthetic

Quality Level

grade

Halal
Kosher

description

Natural occurrence: tea, tomato, wine.

assay

85%

contains

synthetic α-tocopherol as stabilizer

refractive index

n20/D 1.484 (lit.)

bp

250 °C (lit.)

solubility

H2O: insoluble
alcohol: soluble

density

0.97 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

organoleptic

green; floral; woody

SMILES string

C\C(C)=C\CC\C(C)=C\C(O)=O

InChI

1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+

InChI key

ZHYZQXUYZJNEHD-VQHVLOKHSA-N

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General description

Geranic acid is a monoterpenemainly used in flavor, fragrance, cosmetics and agro-industries. In vitro studies show that geranic acid exhibits strong inhibitory activity against Fusarium graminearum and Colletotrichum graminicola, the two main fungal pathogens of maize. It may be responsible for the potent tyrosinase inhibitory activity of lemongrass (Cymbopogon citratus).

Application

Possible uses: orange, tea, mint, ripe fruit and melon notes.

Biochem/physiol Actions

Odor (neat): sweet, floral green, geranium leaf-like, woody with a citrus orange body nuance.
Taste at 20 ppm: sweet, woody, leafy, fruity body with some mouthfeel effects.

Disclaimer

For R&D or non-EU Food use. Not for retail sale.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Dermal - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

271.4 °F - closed cup

flash_point_c

133 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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De novo production of the monoterpenoid geranic acid by metabolically engineered Pseudomonas putida.
Mi J, et al.
Microbial cell factories, 13(1), 170-170 (2014)
U Heyen et al.
Applied and environmental microbiology, 66(7), 3004-3009 (2000-07-06)
Monoterpenes with an unsaturated hydrocarbon structure are mineralized anaerobically by the denitrifying beta-proteobacterium Alcaligenes defragrans. Organic acids occurring in cells of A. defragrans and culture medium were characterized to identify potential products of the monoterpene activation reaction. Geranic acid (E,E-3,7-dimethyl-2,6-octadienoic
D C Alexander et al.
Journal of bacteriology, 176(22), 7079-7084 (1994-11-01)
We report that rfe mutants of wild-type strains of Escherichia coli O7, O18, O75, and O111 did not express O-specific polysaccharide unless the rfe mutation was complemented by a cloned rfe gene supplied in a plasmid. The O polysaccharides in
Tanaya Chatterjee
Biotechnology and applied biochemistry, 39(Pt 3), 303-306 (2004-05-25)
Microbial degradation of geraniol, a natural monoterpene alcohol, was studied using a Rhodococcus sp. strain GR3 isolated from soil. The bioconversion product was identified as geranic acid [(2 E )-3,7-dimethylocta-2,6-dienoic acid] and its structure was established by (1)H-NMR, Fourier-transform IR
Identification of geranic acid, a tyrosinase inhibitor in lemongrass (Cymbopogon citratus).
Masuda T, et al.
Journal of Agricultural and Food Chemistry, 56(2), 597-601 (2007)

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