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geranic acid

Chemical Structure

General Material Information

Preferred name geranic acid
Trivial Name Geranic acid
Short Description 3,7-dimethylocta-2,6-dienoic acid
Formula C10 H16 O2
CAS Number 459-80-3
FEMA Number 4121
Flavis Number 8.081
ECHA Number 207-299-9
FDA UNII PL902IKN0A
Beilstein Number 1763804
MDL MFCD00036493
COE Number 10094
xLogP3-AA 3.10 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1825 (E,Z)-geranic acid
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 459-80-3 ; GERANIC ACID
Synonyms
  • decaprenoic acid
  • 3,7-dimethyl 2,6-octadienoic acid
  • 3,7-dimethyl octa-2,6-dienoic acid
  • 3,7-dimethyl-2,6-octadienoic acid
  • 3,7-dimethylocta-2,6-dienoic acid
  • (E,Z)- geranic acid
  • neric acid
  • 2,6-octadienoic acid, 3,7-dimethyl-
  • 3,7-dimethylocta-2,6-dienoic acid
  • 2,6-Octadienoic acid, 3,7-dimethyl-
  • 3,7-Dimethyl-2,6-octadienoic acid
  • NSC 229335

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

3,7-dimethylocta-2,6-dienoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:459-80-3
Pubchem (cid):9989
Pubchem (sid):134973135
Pherobase:View
Publications by PubMed
Identification of wine aroma precursors in Moscato Giallo grape juice: a nuclear magnetic resonance and liquid chromatography-mass spectrometry tandem study.
Characterization of two geraniol synthases from Valeriana officinalis and Lippia dulcis: similar activity but difference in subcellular localization.
Monitoring tea fermentation/manufacturing by direct analysis in real time (DART) mass spectrometry.
Insecticidal and biting deterrent activity of rose-scented geranium (Pelargonium spp.) essential oils and individual compounds against Stephanitis pyrioides and Aedes aegypti.
Polyamino geranic derivatives as new chemosensitizers to combat antibiotic resistant gram-negative bacteria.
Inhibitory effects of geranic acid derivatives on melanin biosynthesis.
Physiology of deletion mutants in the anaerobic β-myrcene degradation pathway in Castellaniella defragrans.
Growth inhibition of human gynecologic and colon cancer cells by Phyllanthus watsonii through apoptosis induction.
Geraniol and geranial dehydrogenases induced in anaerobic monoterpene degradation by Castellaniella defragrans.
Metabolic engineering of geranic acid in maize to achieve fungal resistance is compromised by novel glycosylation patterns.
Identification of geranic acid, a tyrosinase inhibitor in lemongrass (Cymbopogon citratus).
Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol.
Antitumor effect of geranylamine derivatives on human hepatoma.
Biotransformation of geraniol by Rhodococcus sp. strain GR3.
Toxicity of terpenes to spores and mycelium of Penicillium digitatum.
Geraniol biotransformation-pathway in spores of Penicillium digitatum.
Geranic acid formation, an initial reaction of anaerobic monoterpene metabolism in denitrifying Alcaligenes defragrans.
Mechanism of inhibition of aldehyde dehydrogenase by citral, a retinoid antagonist.
Fractionation of glycoside precursors of aroma in grapes and wine.
Aggregation pheromone for the pepper weevil,Anthonomus eugenii cano (Coleoptera: Curculionidae): Identification and field activity.
Constituents of wing gland and abdominal hair pencil secretions of male African sugarcane borer,Eldana saccharina walker (Lepidoptera: Pyralidae).
Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
Metabolic fate of menthofuran in rats. Novel oxidative pathways.
Catabolism of geraniol by cell suspension cultures of Citrus limon.
Constituents of mandibular and Dufour's glands of an australianPolyrhachis weaver ant.
Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes.
The Nasonov pheromone of the honeybeeApis mellifera L. (Hymenoptera, Apidae). Part II. Bioassay of the components using foragers.
Microbial transformation of terpenoids. I. Identification of metabolites produced by a pseudomonad from citronellal and citral.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
UM BBD:Search
KEGG (GenomeNet):C16461
HMDB (The Human Metabolome Database):HMDB36103
FooDB:FDB014944
Export Tariff Code:2916.19.6000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 168.2359161377
Specific gravity @ 25 °C
Pounds per Gallon 7.922 to 7.972
Refractive Index 1.479 to 1.489 @ 20 °C
Boiling Point 149 to 151°C @ 18 mm Hg
Vapor Pressure 0.000373 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 3.066 est
Solubility
alcohol Yes
propylene glycol Yes
water, 108.2 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Green
dry, weedy, acidic, green, moldy, woody, greasy, sweet
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 272 hour(s) at 100.00 %
Luebke, William tgsc, (2006) At 10.00 % in propylene glycol. dry weedy acidic green moldy feet woody
General comment Green weedy woody greasy sweet
Flavor Type: Green
dry, weedy, musty, green, woody
Luebke, William tgsc, (2006) At 25.00 ppm in water. dry weedy musty green woody
Found in bitter orange and lemon balm, this can be used to balance out sweet notes in those or other citrus formulations. Green

Occurrences

Potential Uses

Applications
Odor purposes Citrus, Geranium, Green, Rose, Woody
Flavoring purposes Tea, Tomato
Other purposes Fixer, Weedy
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 21 - Harmful in contact with skin.
R 38 - Irritating to skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37 - Wear suitable protective clothing and gloves.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Human Experience:
4 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 3700 mg/kg
Food and Cosmetics Toxicology. Vol. 17, Pg. 785, 1979.

oral-mouse LD50 4000 mg/kg
Biochemical Journal. Vol. 34, Pg. 1196, 1940.

Dermal Toxicity:
skin-rabbit LD50 1750 mg/kg
Food and Cosmetics Toxicology. Vol. 17, Pg. 785, 1979.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for geranic acid usage levels up to:
1.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.049 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): ND (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 2200 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 22. Update in publication number(s): 28
Click here to view publication 22
average usual ppmaverage maximum ppm
baked goods: 10.0000050.00000
beverages(nonalcoholic): 3.0000015.00000
beverages(alcoholic): --
breakfast cereal: 5.0000025.00000
cheese: 3.0000015.00000
chewing gum: 165.00000500.00000
condiments / relishes: 5.0000025.00000
confectionery froastings: 10.0000050.00000
egg products: --
fats / oils: 2.0000010.00000
fish products: 2.0000010.00000
frozen dairy: 3.0000015.00000
fruit ices: 3.0000015.00000
gelatins / puddings: 5.0000025.00000
granulated sugar: --
gravies: 15.0000075.00000
hard candy: 100.00000400.00000
imitation dairy: 3.0000015.00000
instant coffee / tea: --
jams / jellies: 5.0000025.00000
meat products: 2.0000010.00000
milk products: 3.0000015.00000
nut products: --
other grains: 5.0000025.00000
poultry: 2.0000010.00000
processed fruits: 2.0000010.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 5.0000025.00000
snack foods: 10.0000050.00000
soft candy: --
soups: 5.0000025.00000
sugar substitutes: --
sweet sauces: 5.0000025.00000
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 2.0000010.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): --
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 15.0000075.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 6, Revision 1 (FGE.06Rev1) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 95 (FGE.95): Consideration of aliphatic, linear or branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters evaluated by JECFA (69th meeting) structurally related to esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids evaluated by EFSA in FGE.05Rev1 (2008)
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):459-80-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9989
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3,7-dimethylocta-2,6-dienoic acid
Chemidplus:0000459803
RTECS:RG5380000 for cas# 459-80-3