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gamma-terpinene

Chemical Structure

General Material Information

Preferred name gamma-terpinene
Trivial Name γ-Terpinene
Short Description p-mentha-1,4-diene
Formula C10 H16
CAS Number 99-85-4
FEMA Number 3559
Flavis Number 1.02
ECHA Number 202-794-6
FDA UNII 4YGF4PQP49
Nikkaji Number J4.974C
Beilstein Number 2038347
MDL MFCD00001537
COE Number 11025
xLogP3-AA 2.80 (est)
NMR Predictor External link
JECFA Food Flavoring 1340 p-mentha-1,4-diene
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 99-85-4 ; GAMMA-TERPINENE
Synonyms
  • crithmene
  • 1,4-cyclohexadiene, 1-methyl-4-(1-methylethyl)-
  • 1,4-cyclohexadiene, 1-methyl-4-isopropyl-
  • p- mentha-1,4-diene
  • para- mentha-1,4-diene
  • 1,4-p- menthadiene
  • 1,4-para- menthadiene
  • 4-methyl-1-(1-methylethyl)-1,4-cyclohexadiene
  • 1-methyl-4-(1-methyl ethyl)-1,4-cyclohexadiene
  • 1-methyl-4-(1-methylethyl)-1,4-cyclohexadiene
  • 1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene
  • 1-methyl-4-isopropyl-1,4-cyclohexadiene
  • 1-methyl-4-propan-2-ylcyclohexa-1,4-diene
  • moslene
  • 4-iso propyl-1-methyl-1,4-cyclohexadiene
  • 1-iso propyl-4-methyl-1,4-cyclohexadiene
  • 1-iso propyl-4-methylcyclohexa-1,4-diene
  • g- terpinene
  • gamma- terpinene 60% ex lemon natural
  • gamma- terpinene 70% ex lemon natural
  • terpinene gamma natural
  • gamma- terpinene natural
  • gamma- terpinene P&F
  • 1-methyl-4-propan-2-ylcyclohexa-1,4-diene
  • 1,4-Cyclohexadiene, 1-methyl-4-(1-methylethyl)-
  • p-Mentha-1,4-diene
  • 1-Methyl-4-(1-methylethyl)-1,4-cyclohexadiene
  • γ-Terpinene
  • γ-Terpinen
  • 4-Isopropyl-1-methyl-1,4-cyclohexadiene
  • 1-Methyl-4-isopropyl-1,4-cyclohexadiene
  • 1-Isopropyl-4-methyl-1,4-cyclohexadiene
  • NSC 21448
  • 1-Methyl-4-(propan-2-yl)cyclohexa-1,4-diene

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

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Literature & References

1-methyl-4-propan-2-ylcyclohexa-1,4-diene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:99-85-4
Pubchem (cid):7461
Pubchem (sid):134972060
Flavornet:99-85-4
Pherobase:View
Publications by PubMed
The chemical composition and the content of volatile oil: potential factors that can contribute to the oxidative stability of Nigella sativa L. crude oil.
Volatile aroma components and antioxidant activities of the flavedo peel extract of unripe Shiikuwasha (Citrus depressa Hayata).
Comparative study on the antioxidant capacity and cholinesterase inhibitory activity of Citrus aurantifolia Swingle, C. aurantium L., and C. bergamia Risso and Poit. peel essential oils.
a-Terpinene, an antioxidant in tea tree oil, autoxidizes rapidly to skin allergens on air exposure.
A comparative study on chemical composition and antioxidant activity of ginger (Zingiber officinale) and cumin (Cuminum cyminum).
Terpene synthases of oregano (Origanum vulgare L.) and their roles in the pathway and regulation of terpene biosynthesis.
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
Flavor components of monoterpenes in citrus essential oils enhance the release of monoamines from rat brain slices.
Character impact odorants of Citrus Hallabong [(C. unshiu Marcov x C. sinensis Osbeck) x C. reticulata Blanco] cold-pressed peel oil.
Characterization of the odor-active volatiles in citrus Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
Volatile flavor components of ripe and overripe ki-mikans (Citrus flaviculpus Hort. ex Tanaka) in comparison with Hyuganatsu (Citrus tamurana Hort. ex Tanaka).
Encapsulation of lemon oil by paste method using beta-cyclodextrin: encapsulation efficiency and profile of oil volatiles.
A comparative study on chemical composition and antioxidant activity of ginger (Zingiber officinale) and cumin (Cuminum cyminum).

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
Metabolomics Database:Search
KEGG (GenomeNet):C09900
HMDB (The Human Metabolome Database):HMDB05806
FooDB:FDB015968
Export Tariff Code:2902.90.3050
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 136.23751831055
Specific gravity @ 25 °C
Pounds per Gallon 7.04 to 7.065
Refractive Index 1.473 to 1.477 @ 20 °C
Boiling Point 181 to 183°C @ 760 mm Hg
Vapor Pressure 1.075 mmHg @ 25 °C
Vapor Density 4.7
Flash Point TCC Value 51.67 °C TCC
logP (o/w) 4.5
Solubility
alcohol Yes
fixed oils Yes
water, 8.68 mg/L @ 22 °C (exp) Yes
water No
Stability
alcoholic fine fragrance Fair
antiperspirant Fair
soap Fair
toiletry application Fair
fabric softener Poor
hypochlorite bleach Poor
liquid detergent Poor
perborate powder detergent Poor

Organoleptic Properties

Odor Type: Terpenic
oily, woody, terpenic, lemon, lime, tropical, herbal, sweet, citrus
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 4 hour(s) at 100.00 %
Luebke, William tgsc, (1989) At 10.00 % in dipropylene glycol. oily woody terpene lemon/lime tropical herbal
Mosciano, Gerard P&F 18, No. 1, 43, (1993) Terpy, sweet, citrus, with tropical and lime nuances
Flavor Type: Terpenic
terpenic, citrus, lime, oily, green, tropical, fruity
Mosciano, Gerard P&F 18, No. 1, 43, (1993) At 40.00 ppm. Terpy, citrus, lime-Iike, oily, green with a tropical fruity nuance

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 10 - Flammable.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
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 37/39 - Wear suitable gloves and eye/face protection.
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:
5 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 [sex: M,F] 3650 mg/kg
(Moreno, 1973ag)

oral-rat LD50 3650 mg/kg
Food and Cosmetics Toxicology. Vol. 14, Pg. 875, 1976.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 14, Pg. 875, 1976.

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 gamma-terpinene usage levels up to:
5.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 1200.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 321.00 (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: 11
Click here to view publication 11
average usual ppmaverage maximum ppm
baked goods: -13.60000
beverages(nonalcoholic): -8.50000
beverages(alcoholic): -10.00000
breakfast cereal: --
cheese: --
chewing gum: -25.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -8.60000
fruit ices: --
gelatins / puddings: -8.60000
granulated sugar: --
gravies: --
hard candy: -50.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -20.00000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: -10.30000
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 25, (FGE.25)[1] - Aliphatic and aromatic hydrocarbons from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 78 (FGE.78)[1] - Consideration of Aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25 - Scientific Opinion of the 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 25Rev1: Aliphatic and aromatic hydrocarbons from chemical group 31
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 78, Revision 1 (FGE.78Rev1): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic and aromatic hydrocarbons evaluated by EFSA in FGE.25Rev2
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 25, Revision 2 (FGE.25Rev2): Aliphatic and aromatic hydrocarbons from chemical group 31
View page or View pdf

Scientific Opinion on the safety and efficacy of aliphatic and aromatic hydrocarbons (chemical group 31) when used as flavourings for all animal species
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 78, Revision 2 (FGE.78Rev2): Consideration of aliphatic and alicyclic and aromatic hydrocarbons evaluated by JECFA (63rd meeting) structurally related to aliphatic hydrocarbons evaluated by EFSA in FGE.25Rev3
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):99-85-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7461
National Institute of Allergy and Infectious Diseases:Data
SCCNFP:opinion
WISER:UN 2319
WGK Germany:2
1-methyl-4-propan-2-ylcyclohexa-1,4-diene
Chemidplus:0000099854
RTECS:OS8070000 for cas# 99-85-4