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Merck

W412101

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
Flavis number:
8.081
PubChem Substance ID:
24901980
UNSPSC Code:
12164502
FEMA Number:
4121
NACRES:
NA.21
EC Number:
207-299-9
MDL number:
MFCD00036493
Beilstein/REAXYS Number:
1763804
Organoleptic:
green; floral; woody
Grade:
Halal, Kosher
Biological source:
synthetic
Food allergen:
no known allergens

Key Documents

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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+

SMILES string

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

InChI key

ZHYZQXUYZJNEHD-VQHVLOKHSA-N

biological source

synthetic

grade

Halal, Kosher

assay

85%

contains

synthetic α-tocopherol as stabilizer

Quality Level

300, 400

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

description

Natural occurrence: tea, tomato, wine.

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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

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBS7610
SHBR4521
SHBS0441
SHBQ4299
SHBP2193

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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)
Toshiya Masuda et al.
Journal of agricultural and food chemistry, 56(2), 597-601 (2007-12-18)
Lemongrass is a popular Asian herb having a lemon-like flavor. Very recently, potent tyrosinase inhibitory activity has been found in lemongrass in addition to various biological activities reported in the literature. The aim of the present study is to identify
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
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
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