geranic acid
3,7-dimethylocta-2,6-dienoic acid
Identification
| Name | geranic acid |
| IUPAC | 3,7-dimethylocta-2,6-dienoic acid |
| CAS Number | 459-80-3 |
| EINECS | 207-299-9 |
| FDA UNII | PL902IKN0A |
| Molecular Formula | C10 H16 O2 |
| Molecular Weight | 168.23592000 |
| MDL Number | MFCD00036493 |
| Beilstein | 1763804 |
| CoE Number | 10094 |
Regulatory
| JECFA Food Flavoring | 1825 (E,Z)-geranic acid |
| DG SANTE Food Flavourings | 08.081 geranic acid |
| FEMA Number | 4121 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 459-80-3 ; GERANIC ACID |
Physical Properties
| Appearance | colorless to pale yellow clear oily liquid (est) |
| Assay | 95.00 to 100.00 sum of isomers |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.95200 to 0.95800 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.922 to 7.972 |
| Refractive Index | 1.47900 to 1.48900 @ 20.00 °C. |
| Melting Point | 21.00 °C. @ 760.00 mm Hg |
| Boiling Point | 250.00 °C. @ 760.00 mm Hg, 149.00 to 151.00 °C. @ 18.00 mm Hg |
| Vapor Pressure | 0.000373 mmHg @ 25.00 °C. (est) |
| Flash Point | 230.00 °F. TCC ( 110.00 °C. ) |
| logP (o/w) | 3.066 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Strength | medium , |
| Substantivity | 272 hour(s) at 100.00 % |
| Odor Description |
at 10.00 % in propylene glycol. green weedy woody greasy sweet Green, floral, weedy, woody notes
|
| Odor sample from | Sigma-Aldrich |
| Taste Description |
at 25.00 ppm in water. green
|
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Human Experience | 4 % solution: no irritation or sensitization. |
| Oral/Parenteral Toxicity | oral-rat LD50 3700 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 1750 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| 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 |
| baked goods | 10.00000 |
| beverages(nonalcoholic) | 3.00000 |
| beverages(alcoholic) | - |
| breakfast cereal | 5.00000 |
| cheese | 3.00000 |
| chewing gum | 165.00000 |
| condiments / relishes | 5.00000 |
| confectionery froastings | 10.00000 |
| egg products | - |
| fats / oils | 2.00000 |
| fish products | 2.00000 |
| frozen dairy | 3.00000 |
| fruit ices | 3.00000 |
| gelatins / puddings | 5.00000 |
| granulated sugar | - |
| gravies | 15.00000 |
| hard candy | 100.00000 |
| imitation dairy | 3.00000 |
| instant coffee / tea | - |
| jams / jellies | 5.00000 |
| meat products | 2.00000 |
| milk products | 3.00000 |
| nut products | - |
| other grains | 5.00000 |
| poultry | 2.00000 |
| processed fruits | 2.00000 |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | 5.00000 |
| snack foods | 10.00000 |
| soft candy | - |
| soups | 5.00000 |
| sugar substitutes | - |
| sweet sauces | 5.00000 |
| Dairy products, excluding products of category 02.0 (01.0) | 3.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 2.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 3.00000 |
| Processed fruit (04.1) | 2.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 5.00000 |
| Bakery wares (07.0) | 10.00000 |
| Meat and meat products, including poultry and game (08.0) | 2.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 2.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 10.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | - |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 10.00000 |
| Ready-to-eat savouries (15.0) | 15.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 5.00000 |
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Potential Uses
Natural Occurrence
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-
PubMed:
Identification of wine aroma precursors in Moscato Giallo grape juice: a nuclear magnetic resonance and liquid chromatography-mass spectrometry tandem study.
PubMed:
Characterization of two geraniol synthases from Valeriana officinalis and Lippia dulcis: similar activity but difference in subcellular localization.
PubMed:
Monitoring tea fermentation/manufacturing by direct analysis in real time (DART) mass spectrometry.
PubMed:
Insecticidal and biting deterrent activity of rose-scented geranium (Pelargonium spp.) essential oils and individual compounds against Stephanitis pyrioides and Aedes aegypti.
PubMed:
Polyamino geranic derivatives as new chemosensitizers to combat antibiotic resistant gram-negative bacteria.
PubMed:
Inhibitory effects of geranic acid derivatives on melanin biosynthesis.
PubMed:
Physiology of deletion mutants in the anaerobic β-myrcene degradation pathway in Castellaniella defragrans.
PubMed:
Growth inhibition of human gynecologic and colon cancer cells by Phyllanthus watsonii through apoptosis induction.
PubMed:
Geraniol and geranial dehydrogenases induced in anaerobic monoterpene degradation by Castellaniella defragrans.
PubMed:
Metabolic engineering of geranic acid in maize to achieve fungal resistance is compromised by novel glycosylation patterns.
PubMed:
Identification of geranic acid, a tyrosinase inhibitor in lemongrass (Cymbopogon citratus).
PubMed:
Utilization of geraniol is dependent on molybdenum in Pseudomonas aeruginosa: evidence for different metabolic routes for oxidation of geraniol and citronellol.
PubMed:
Antitumor effect of geranylamine derivatives on human hepatoma.
PubMed:
Biotransformation of geraniol by Rhodococcus sp. strain GR3.
PubMed:
Toxicity of terpenes to spores and mycelium of Penicillium digitatum.
PubMed:
Geraniol biotransformation-pathway in spores of Penicillium digitatum.
PubMed:
Geranic acid formation, an initial reaction of anaerobic monoterpene metabolism in denitrifying Alcaligenes defragrans.
PubMed:
Mechanism of inhibition of aldehyde dehydrogenase by citral, a retinoid antagonist.
PubMed:
Fractionation of glycoside precursors of aroma in grapes and wine.
PubMed:
Aggregation pheromone for the pepper weevil,Anthonomus eugenii cano (Coleoptera: Curculionidae): Identification and field activity.
PubMed:
Constituents of wing gland and abdominal hair pencil secretions of male African sugarcane borer,Eldana saccharina walker (Lepidoptera: Pyralidae).
PubMed:
Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
PubMed:
Metabolic fate of menthofuran in rats. Novel oxidative pathways.
PubMed:
Catabolism of geraniol by cell suspension cultures of Citrus limon.
PubMed:
Constituents of mandibular and Dufour's glands of an australianPolyrhachis weaver ant.
PubMed:
Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes.
PubMed:
The Nasonov pheromone of the honeybeeApis mellifera L. (Hymenoptera, Apidae). Part II. Bioassay of the components using foragers.
PubMed:
Microbial transformation of terpenoids. I. Identification of metabolites produced by a pseudomonad from citronellal and citral.