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459-80-3

459-80-3 Structure

459-80-3 Structure
IdentificationMore
[Name]

GERANIC ACID
[CAS]

459-80-3
[Synonyms]

3,7-DIMETHYL-2,6-OCTADIENOIC ACID
GERANIC ACID
RARECHEM AL BO 0140
(2E)-3,7-Dimethyl-2,6-octadienoic acid
3,7-dimethyl-2,6(and2,7)-octadienoicacid
3,7-dimethyl-6-octadienoicacid
6-Octadienoicacid,3,7-dimethyl-2
geranic acid, mixture of isomers
3,7-dimethylocta-2,6-dienoic acid
GERANIC ACID, TECH., 85%, MIXTURE OF ISO MERS
2,6-Octadienoic acid, 3,7-dimethyl-
3,7-dimethyl-2,6-octadenoic acid
decaprenoic acid
GERANID
[EINECS(EC#)]

207-299-9
[Molecular Formula]

C10H16O2
[MDL Number]

MFCD00036493
[Molecular Weight]

168.23
[MOL File]

459-80-3.mol
Chemical PropertiesBack Directory
[Melting point ]

185-186 °C (decomp)
[Boiling point ]

250 °C(lit.)
[density ]

0.97 g/mL at 25 °C(lit.)
[FEMA ]

4121
[refractive index ]

n20/D 1.484(lit.)
[Fp ]

>230 °F
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

H2O: insoluble
[form ]

liquid
[pka]

5.17±0.33(Predicted)
[color ]

Colorless liquid, slightly viscous, and increasing in viscosity with age or exposure to air and daylight.
[Odor]

at 10.00 % in propylene glycol. dry weedy acidic green moldy feet woody
[biological source]

synthetic
[Odor Type]

green
[Water Solubility ]

H2O: insoluble
alcohol: soluble
[JECFA Number]

1825
[BRN ]

1763804
[Cosmetics Ingredients Functions]

pH ADJUSTERS
FRAGRANCE
PERFUMING
DEODORANT
FLAVOURING
[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+
[InChIKey]

ZHYZQXUYZJNEHD-VQHVLOKHSA-N
[SMILES]

C\C(C)=C\CC\C(C)=C\C(O)=O
[LogP]

3.46
[CAS DataBase Reference]

459-80-3(CAS DataBase Reference)
[EPA Substance Registry System]

2,6-Octadienoic acid, 3,7-dimethyl- (459-80-3)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H312-H315
[Precautionary statements ]

P264-P280-P302+P352+P312-P332+P313-P362+P364-P501
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R21:Harmful in contact with skin.
R38:Irritating to the skin.
[Safety Statements ]

S36/37:Wear suitable protective clothing and gloves .
[WGK Germany ]

3
[RTECS ]

RG5380000
[F ]

10
[Hazard Note ]

Irritant
[TSCA ]

Yes
[HS Code ]

2916199590
[Storage Class]

10 - Combustible liquids
[Hazard Classifications]

Acute Tox. 4 Dermal
Skin Irrit. 2
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium hydroxide-->Ethyl acetate-->Diethyl ether-->Ethyl bromoacetate-->Triethyl phosphite-->6-Methyl-5-hepten-2-one-->Lycopene-->ETHYL GERANATE-->GERANIOL-->2,6-Octadienal, 3,7-dimethyl-, (E)--->Citral-->Butyraldehyde-->NEROL-->Acetic anhydride
[Preparation Products]

Damascenone-->CITRONELLIC ACID
Hazard InformationBack Directory
[Chemical Properties]

Colorless viscous liquid; neat; sweet, foral green, geranium leafike, woody with a citrus orange body nuance.
[Occurrence]

Reported found in tea, tomato and wine
[Uses]

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

ChEBI: Geranic acid is a polyunsaturated fatty acid that is octa-2,6-dienoic acid bearing two methyl substituents at positions 3 and 7 (the 2E-isomer). It has a role as a pheromone, an EC 1.14.18.1 (tyrosinase) inhibitor, a plant metabolite, an antifungal agent and a melanin synthesis inhibitor. It is a polyunsaturated fatty acid, a methyl-branched fatty acid, a monoterpenoid and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a geranate.
[Production Methods]

Geranic acidacid is produced
1) from 2-Methylhepten-2-one-6 with Iodoor Bromoacetic ester and a Zinc type catalyst.
2) by oxidation of Citral.
[Aroma threshold values]

Medium strength odor, green type; recommend smelling in a 10.0% solution or less.
[Taste threshold values]

Sweet, woody, leafy, fruity body with some mouthfeel effects at 20 ppm.
[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).
[Biochem/physiol Actions]

Odor (neat): sweet, floral green, geranium leaf-like, woody with a citrus orange body nuance.
Spectrum DetailBack Directory
[Spectrum Detail]

GERANIC ACID(459-80-3)IR
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

Geranic acid(459-80-3)
[Sigma Aldrich]

459-80-3(sigmaaldrich)
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Tags:459-80-3 Related Product Information
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