EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

geranic acid
3,7-dimethylocta-2,6-dienoic acid

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Name:3,7-dimethylocta-2,6-dienoic acid
CAS Number: 459-80-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-299-9
FDA UNII:PL902IKN0A
Beilstein Number:1763804
MDL:MFCD00036493
CoE Number:10094
XlogP3-AA:3.10 (est)
Molecular Weight:168.23592000
Formula:C10 H16 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Also(can) Contains:(E)-geranic acid
 (Z)-geranic acid
EFSA/JECFA Comments:
JECFA evaluated (E,Z)-Geranic acid, a mixture of 49.4 % (E)-isomer and 45.6 % (Z)-isomer.
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:1825 (E,Z)-geranic acid
FLAVIS Number:08.081 (Old)
DG SANTE Food Flavourings:08.081 geranic acid
FEMA Number:4121 geranic acid
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: 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
Boiling Point: 149.00 to 151.00 °C. @ 18.00 mm Hg
Vapor Pressure:0.000373 mm/Hg @ 25.00 °C. (est)
Flash Point: 230.00 °F. TCC ( 110.00 °C. )
logP (o/w): 3.066 (est)
Soluble in:
 alcohol
 propylene glycol
 water, 108.2 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: green
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
Substantivity:272 hour(s) at 100.00 %
dry weedy acidic green moldy woody
Odor Description:at 10.00 % in propylene glycol. dry weedy acidic green moldy feet woody
Luebke, William tgsc, (2006)
Odor sample from: Sigma-Aldrich
green weedy woody greasy sweet
Odor Description:green weedy woody greasy sweet
Flavor Type: green
dry weedy musty green woody
Taste Description: at 25.00 ppm in water. dry weedy musty green woody
Luebke, William tgsc, (2006)
Odor and/or flavor descriptions from others (if found).
Bedoukian Research
GERANIC ACID ≥90.0% (sum of isomers), Kosher
Odor Description:Green, floral, weedy, woody notes
The soft, fresh, green-floral odor is useful for reconstituted oils.
Taste Description:green
Found in bitter orange and lemon balm, this can be used to balance out sweet notes in those or other citrus formulations.
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
Bedoukian Research
GERANIC ACID
≥90.0% (sum of isomers), Kosher
Odor: Green, floral, weedy, woody notes
Use: The soft, fresh, green-floral odor is useful for reconstituted oils.
Flavor: green
Found in bitter orange and lemon balm, this can be used to balance out sweet notes in those or other citrus formulations.
BOC Sciences
For experimental / research use only.
GERANIC ACID 95.0% (sum of isomers)
Global Essence
Geranic Acid
Kingchem Laboratories
GERANIC ACID
Odor: Green, floral note with wood undertones
Lluch Essence
GERANIC ACID 95%
Nagar Haveli Perfumes & Aromatics
Geranic Acid
Odor: dry weedy acidic green moldy feet woody greasy
Nagar Haveli Perfumes & Aromatics
Geranic Acid
Natural
Odor: dry weedy acidic green moldy feet woody greasy
PCAS
Geranic Acid
Penta International
GERANIC ACID, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
Geranic Acid
Sigma-Aldrich
Geranic acid, 85%, stabilised
Odor: lemon; rose; woody; wine-like
Certified Food Grade Products
Synerzine
Geranic Acid
 
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
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
 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
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
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
 
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
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (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
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
No odor group found for these
octanal propylene glycol acetal
FL/FR
aldehydic
aldehydic
green hexanal
FL/FR
balsamic
betula pubescens bud oil
FL/FR
hemlock western oil (tsuga heterophylla) canada
FR
spruce needle absolute
FL/FR
valerian rhizome absolute
FL/FR
citrus
citronella oil java
FR
alpha-
methylene citronellal
FR
neroli ketone
FR
valencene
FL/FR
dry
autumn specialty
FR
earthy
2-
octanone
FL/FR
scotch
pine needle oil
FL/FR
scotch
pine needle oil estonia
FL/FR
scotch
pine needle oil yugoslavia
FL/FR
fatty
5-
methyl-5-hexen-2-one
FL/FR
floral
cassie absolute
FL/FR
cassie concrete
FR
gardenia oxide
FR
karo karounde absolute
FR
linalool
FL/FR
beta-
ocimene
FL/FR
orange leaf absolute
FL/FR
styralyl propionate
FL/FR
tuberose acetate
FR
fruity
apple ketal
FL/FR
alpha,alpha-
dimethyl benzyl isobutyrate
FL/FR
green acetate
FR
2-
nonanone
FL/FR
green
bergoxane
FR
alpha-
elemol
FL/FR
fresh nitrile
FR
galbanum absolute replacer
FR
galbanum oil
FL/FR
galbanum oleoresin
FL/FR
galbanum resinoid
FL/FR
iso
green methanoindene
FR
(E)-2-
hexen-1-yl salicylate
FR
leafy oxime
FR
para-
methyl hydratropaldehyde
FL/FR
oakmoss oil
FR
iso
propyl quinoline
FR
terpinyl propionate
FL/FR
3,5,5-
trimethyl hexanol
FL/FR
valerian rhizome oil CO2 extract china
FL/FR
herbal
bornyl salicylate
FR
(+)-alpha-
campholenic aldehyde
FL/FR
canarium luzonicum oil
FL/FR
clary sage oil france
FL/FR
iso
dihydrolavandulal
FL/FR
herbal ketone
FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
linalyl octanoate
FL/FR
nonisyl formate
FR
3-
octyl acetate
FL/FR
valerian rhizome oil
FL/FR
melon
(Z)-6-
nonenal
FL/FR
minty
(-)-iso
pulegol
FL/FR
spearmint absolute
FL/FR
mossy
oakmoss absolute
FL/FR
nutty
2-
ethyl pyrazine
FL/FR
orris
iso
eugenyl formate
FL/FR
spicy
cuminyl nitrile
FR
iso
cyclogeraniol (IFF)
FR
methyl heptadienone
FL/FR
2-
octanol
FL/FR
For Flavor
No flavor group found for these
betula pubescens bud oil
FL/FR
alpha-
elemol
FL/FR
iso
eugenyl formate
FL/FR
octanal propylene glycol acetal
FL/FR
scotch
pine needle oil
FL/FR
scotch
pine needle oil estonia
FL/FR
scotch
pine needle oil yugoslavia
FL/FR
balsamic
balsamic
spruce needle absolute
FL/FR
camphoreous
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
cheesy
2-
nonanone
FL/FR
citrus
linalool
FL/FR
styralyl propionate
FL/FR
valencene
FL/FR
dairy
2-
octanone
FL/FR
ethereal
5-
methyl-5-hexen-2-one
FL/FR
fatty
(E)-2-
octenoic acid
FL
floral
orange leaf absolute
FL/FR
fruity
apple ketal
FL/FR
alpha,alpha-
dimethyl benzyl isobutyrate
FL/FR
linalyl octanoate
FL/FR
valerian rhizome absolute
FL/FR
valerian rhizome oil
FL/FR
valerian rhizome oil CO2 extract china
FL/FR
green
(+)-alpha-
campholenic aldehyde
FL/FR
canarium luzonicum oil
FL/FR
galbanum oil
FL/FR
galbanum oleoresin
FL/FR
galbanum resinoid
FL/FR
methyl heptadienone
FL/FR
para-
methyl hydratropaldehyde
FL/FR
(Z)-6-
nonenal
FL/FR
oakmoss absolute
FL/FR
beta-
ocimene
FL/FR
3-
octyl acetate
FL/FR
terpinyl propionate
FL/FR
3,5,5-
trimethyl hexanol
FL/FR
herbal
clary sage oil france
FL/FR
iso
dihydrolavandulal
FL/FR
green hexanal
FL/FR
minty
(-)-iso
pulegol
FL/FR
spearmint absolute
FL/FR
nutty
2-
ethyl pyrazine
FL/FR
spicy
cassie absolute
FL/FR
2-
octanol
FL/FR
vegetable
alpha-
benzylidene methional
FL
 
Potential Uses:
FRcitrus
 fixer
FRgeranium
FRgreen
FRrose
FLtea
FLtomato
 weedy
FRwoody
 
Occurrence (nature, food, other):note
 bay leaf oil lemon @ 0.1%
Data GC Search Trop Picture
 bay leaf oil lemon @ 1.0%
Data GC Search Trop Picture
 callitris glaucophylla wood oil australia @ 3.90%
Data GC Search Trop Picture
 callitris intratropica wood oil australia @ 0.20%
Data GC Search Trop Picture
 callitris intratropica wood oil australia @ 0.90%
Data GC Search Trop Picture
 cardamom fruit
Search Trop Picture
 cardamom seed
Search Trop Picture
 champaca concrete @ 0.10%
Data GC Search Trop Picture
 cistus oil @ 2.4%
Data GC Search Trop Picture
 lemon balm shoot
Search Trop Picture
 lemon verbena oil morocco @ 0.7%
Data GC Search Trop Picture
 lemongrass oil morocco @ 0.10%
Data GC Search Trop Picture
 lemongrass oil morocco @ 1.40%
Data GC Search Trop Picture
 lemongrass plant
Search Trop Picture
 melissa oil slovak republic @ 1.05%
Data GC Search Trop Picture
 peppermint leaf
Search Trop Picture
 pimenta racemosa leaf oil lemon @ 0.07%
Data GC Search Trop Picture
 tea
Search Trop Picture
 tomato
Search Trop Picture
 walnut english walnut leaf
Search Trop Picture
 wine
Search Picture
 wormseed oil spain @ 0.04%
Data GC Search Trop Picture
 
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-
 

Articles:

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.
 
Notes:
synthetic isoprenoid. Present in petitgrain, lemongrass and other essential oils
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