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3,7-dimethyl-6-octenoic acid

Chemical Structure

General Material Information

Preferred name 3,7-dimethyl-6-octenoic acid
Trivial Name Citronellic acid
Short Description citronellic acid
Formula C10 H18 O2
CAS Number 502-47-6
Deleted CAS Number 57030-77-0
FEMA Number 3142
Flavis Number 8.036
ECHA Number 207-939-7
FDA UNII 1JJT408R87
Nikkaji Number J11.776E
Beilstein Number 1722960
MDL MFCD00002728
COE Number 616
xLogP3-AA 3.00 (est)
NMR Predictor External link
JECFA Food Flavoring 1221 3,7-dimethyl-6-octenoic acid
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 502-47-6 ; 3,7-DIMETHYL-6-OCTENOIC ACID
Synonyms
  • citonellic acid
  • citronellic acid
  • (±)- citronellic acid
  • citronellicacid
  • citronellyl acid
  • (±)-3,7-dimethyl-6-octenoic acid
  • 3,7-dimethyl-6-octenoic acid
  • 3,7-dimethyl-oct-6-enoic acid
  • 3,7-dimethyloct-6-enoic acid
  • 6-octenoic acid, 3,7-dimethyl-
  • rhodinolic acid
  • 3,7-dimethyloct-6-enoic acid
  • 6-Octenoic acid, 3,7-dimethyl-
  • Rhodinic acid

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

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Literature & References

3,7-dimethyloct-6-enoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:502-47-6
Pubchem (cid):10402
Pubchem (sid):134978591
Pherobase:View
Publications by PubMed
Biotransformations of terpenes by fungi from Amazonian citrus plants.
Bioefficacy of acyclic monoterpenes and their saturated derivatives against the West Nile vector Culex pipiens.
Inhibitory effects of geranic acid derivatives on melanin biosynthesis.
A piperidine chiron for the Veratrum alkaloids.
Environmental concentrations of methoprene and its transformation products after the treatment of Altosid® XR Briquets in the city of Richmond, British Columbia, Canada.
Fumigant toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae).
Topical toxicity of essential oils to the German cockroach (Dictyoptera: Blattellidae).
Oxidation of citronellal to citronellic acid by molecular oxygen using supported gold catalysts.
Efficacy of botanical extracts from Callitris glaucophylla, against Aedes aegypti and Culex annulirostris mosquitoes.
Malate:quinone oxidoreductase (MqoB) is required for growth on acetate and linear terpenes in Pseudomonas citronellolis.
Inhibition of citrus postharvest pathogens by vapor of citral and related compounds in culture.
Insecticidal activity of monoterpenoids to western corn rootworm (Coleoptera: Chrysomelidae), twospotted spider mite (Acari: Tetranychidae), and house fly (Diptera: Muscidae).
Isolation and characterization of Pseudomonas aeruginosa mutants deficient in the utilization of the terpenoid citronellic acid.
Catabolism of geraniol by cell suspension cultures of Citrus limon.
Metabolism of citral, an alpha,beta-unsaturated aldehyde, in male F344 rats.
Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes.
Biodegradation of acyclic isoprenoids by Pseudomonas species.
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
CHEBI:View
CHEMBL:View
UM BBD:Search
KEGG (GenomeNet):C16462
HMDB (The Human Metabolome Database):HMDB35837
FooDB:FDB014607
Export Tariff Code:2916.19.5000
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 170.25186157227
Specific gravity @ 20 °C
Pounds per Gallon 7.706 to 7.731
Refractive Index 1.452 to 1.455 @ 20 °C
Boiling Point 121 to 122°C @ 1 mm Hg
Vapor Pressure 0.005 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 3.159 est
Solubility
alcohol Yes
water, slightly Yes
water, 89.48 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Green
green, grassy, smoky, fatty, floral, waxy, citronella, vegetable, tobacco
General comment At 10.00 % in dipropylene glycol. green grassy smoky fatty floral
Mosciano, Gerard P&F 25, No. 6, 26, (2000) At 1.00 %. Fatty, waxy, heavy, floral with a slight citronella nuance. It also has vegetative and tobacco nuances
Flavor Type: Floral
floral, rose, fruity, melon, citronella, citrus
Mosciano, Gerard P&F 25, No. 6, 26, (2000) At 5.00 - 30.00 ppm. Mild, floral, rosy, fruity melon with slight hints of citronella and citrus

Occurrences

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 - Avoid contact with skin.
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:
2 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 2610 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 653, 1982.

Dermal Toxicity:
skin-rabbit LD50 450 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 653, 1982.

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 3,7-dimethyl-6-octenoic acid usage levels up to:
2.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 2.70 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.20 (μg/capita/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: 4
Click here to view publication 4
average usual ppmaverage maximum ppm
baked goods: -0.50000
beverages(nonalcoholic): -0.50000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -0.50000
fruit ices: -0.50000
gelatins / puddings: -0.50000
granulated sugar: --
gravies: --
hard candy: -0.50000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

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 72 (FGE.72): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids. Esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2 (2010)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 72, Revision 1 (FGE.72Rev1): Consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids, and related esters evaluated by the JECFA (61st meeting) structurally related to branched- and straight-chain unsaturated carboxylic acids, esters of these and straight-chain aliphatic saturated alcohols evaluated by EFSA in FGE.05Rev2
View page or View pdf

Safety and efficacy of non-conjugated and accumulated unsaturated straight-chain and branched-chain, aliphatic primary alcohols, aldehydes, acids, acetals and esters belonging to chemical group 4 when used as flavourings for all animal species
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 72, Revision 2 (FGE.72Rev2): consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters evaluated by JECFA (61st, 68th and 69th meetings) and structurally related to flavouring substances in FGE.05Rev3
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):502-47-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10402
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 2810
WGK Germany:3
3,7-dimethyloct-6-enoic acid
Chemidplus:0000502476
RTECS:RH3230000 for cas# 502-47-6