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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:
459-80-3
Molecular Weight:
168.23
FEMA Number:
4121
Beilstein/REAXYS Number:
1763804
EC Number:
207-299-9
MDL number:
MFCD00036493
UNSPSC Code:
12164502
PubChem Substance ID:
24901980
Flavis number:
8.081
NACRES:
NA.21

biological source

synthetic

Quality Level

400

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
GHS07

signalword

Warning

hcodes

H312,H315

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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
W A Wolken et al.
Applied microbiology and biotechnology, 57(5-6), 731-737 (2002-01-10)
Spores of Penicillium digitatum ATCC 201167 transform geraniol, nerol, citral, and geranic acid into methylheptenone. Spore extracts of P. digitatum convert geraniol and nerol NAD+-dependently into citral. Spore extract also converts citral NAD+-dependently into geranic acid. Furthermore, a novel enzymatic
Jean Michel Brunel et al.
Bioorganic & medicinal chemistry, 21(5), 1174-1179 (2013-01-29)
Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate reagent (BOP) serves as an efficient and versatile coupling reagent for the design and synthesis of new polyamino geranic acid derivatives in moderate to good chemical yields varying from 47% to 83%. These compounds induced a significant decrease
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