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delta-3-carene

Chemical Structure

General Material Information

Preferred name delta-3-carene
Trivial Name 3-Carene
Short Description d-3-carene
Formula C10 H16
CAS Number 13466-78-9
Deleted CAS Number 116783-27-8
FEMA Number 3821
Flavis Number 1.029
ECHA Number 236-719-3
FDA UNII H2M15SNR6N
Nikkaji Number J8.118C
Beilstein Number 1902766
MDL MFCD00001315
COE Number 10983
xLogP3-AA 2.80 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1342 d-3-carene
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 13466-78-9 ; 3-CARENE
Synonyms
  • (±)-3-carene
  • (±)-delta3-carene
  • 3-carene
  • d-3-carene
  • delta(sup3)- carene
  • S-3-carene
  • delta 3-carene 90 PF
  • delta-3-carene 90 PF
  • 3-carene delta natural
  • delta-3-carene natural
  • carene-3 delta
  • 3,7,7-trimethyl bicyclo(4.1.0)hept-3-ene
  • 3,7,7-trimethyl bicyclohept-3-ene
  • 3,7,7-trimethyl-3-norcarene
  • 3,7,7-trimethylbicyclo[4.1.0]hept-3-ene
  • 3,7,7-trimethylbicyclo[4.1.0]hept-3-ene
  • Bicyclo[4.1.0]hept-3-ene, 3,7,7-trimethyl-
  • 3-Carene
  • Δ3-Carene
  • δ-3-Carene
  • (±)-3-Carene
  • (±)-Δ3-Carene

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

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Literature & References

3,7,7-trimethylbicyclo[4.1.0]hept-3-ene
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:13466-78-9
Pubchem (cid):26049
Pubchem (sid):134991010
Flavornet:13466-78-9
Pherobase:View
Publications by PubMed
Chemical composition of essential oils from the leaves and stem barks of Vietnamese species of Polyalthia harmandiiPolyalthia jucunda and Polyalthia thorelii.
Chemical analysis and calcium channel blocking activity of the essential oil of Perovskia abrotanoides.
Growth-Inhibiting and morphostructural effects of constituents identified in Asarum heterotropoides root on human intestinal bacteria.
Distillation time modifies essential oil yield, composition, and antioxidant capacity of fennel (Foeniculum vulgare Mill).
Sensitive monitoring of monoterpene metabolites in human urine using two-step derivatisation and positive chemical ionisation-tandem mass spectrometry.
Volatile constituents of Pinus roxburghii from Nepal.
Antioxidant and antibacterial activities of crude extracts and essential oils of Syzygium cumini leaves.
Needle removal by pine sawfly larvae increases branch-level VOC emissions and reduces below-ground emissions of Scots pine.
Chemical analysis and biological activities of Cupressus sempervirens var. horizontalis essential oils.
Analysis of the essential oil of large cardamom (Amomum subulatum Roxb.) growing in different agro-climatic zones of Himachal Pradesh, India.
Chemical composition and in vitro evaluation of antimicrobial and anti-acetylcholinesterase properties of the flower oil of Ferula lutea.
Exposure to Anacardiaceae volatile oils and their constituents induces lipid peroxidation within food-borne bacteria cells.
A tale of two carenes: intrinsic optical activity and large-amplitude nuclear displacement.
Plant secondary chemistry mediates the performance of a nutritional symbiont associated with a tree-killing herbivore.
Intraspecific chemical variability of essential oil from leaves of Cupressus atlantica Gaussen, an endemic and endangered coniferous species in Morocco.
Degradation of terpenes and terpenoids from Mediterranean rangelands by mixed rumen bacteria in vitro.
Quantitative evaluation of (+)-Δ(3)-carene metabolites from living larvae of Spodoptera litura by headspace solid-phase microextraction.
Predictors of monoterpene exposure in the Danish furniture industry.
In vitro efficacy of the essential oil of Piper cubeba L. (Piperaceae) against Schistosoma mansoni.
Chemical composition and antioxidant activity of the essential oil of Juniperus phoenicea L. berries.
Citrus essential oil of Nigeria. Part V: Volatile constituents of sweet orange leaf oil (Citrus sinensis).
Insecticidal activity of the essential oil from fruits and seeds of Schinus terebinthifolia Raddi against African malaria vectors.
Reciprocal interactions between the bark beetle-associated yeast Ogataea pini and host plant phytochemistry.
Determination of the chemical composition and in vitro antioxidant activities of essential oil and methanol extracts of Echinophora platyloba DC.
Both gas chromatography and an electronic nose reflect chemical polymorphism of juniper shrubs browsed or avoided by sheep.
Do multiple herbivores maintain chemical diversity of Scots pine monoterpenes?
Mass spectrometric characterization of isomeric terpenoic acids from the oxidation of α-pinene, β-pinene, d-limonene, and Δ3-carene in fine forest aerosol.
α-Pinene- and β-myrcene-rich volatile fruit oil of Cupressus arizonica Greene from northwest Iran.
Survey of ex situ fruit and leaf volatiles from several Pistacia cultivars grown in California.
Comparison of volatile components in Chinese traditional pickled peppers using HS-SPME-GC-MS, GC-O and multivariate analysis.
Interactions between the yeast Ogataea pini and filamentous fungi associated with the western pine beetle.
Chemosensory irritations and pulmonary effects of acute exposure to emissions from oriented strand board.
Development and validation by accuracy profile of a method for the analysis of monoterpenes in indoor air by active sampling and thermal desorption-gas chromatography-mass spectrometry.
The essential oil of Brazilian pepper, Schinus terebinthifolia Raddi in larval control of Stegomyia aegypti (Linnaeus, 1762).
Evolution of the volatile compounds of ripened sausages as a function of both storage time and composition of packaging atmosphere.
Real time in situ detection of organic nitrates in atmospheric aerosols.
Changes in monoterpene emission rates of Quercus ilex infested by aphids tended by native or invasive Lasius ant species.
Inhibition of predator attraction to kairomones by non-host plant volatiles for herbivores: a bypass-trophic signal.
Cytotoxicity and genotoxicity in human lung epithelial A549 cells caused by airborne volatile organic compounds emitted from pine wood and oriented strand boards.
The influence of organ, season and drying method on chemical composition and antioxidant and antimicrobial activities of Juniperus phoenicea L. essential oils.
Regio- and stereoselective oxidation of (+)-Delta(3)-carene by the larvae of common cutworm (Spodoptera litura).
Chemotypes of Pistacia atlantica leaf essential oils from Algeria.
Attraction of Anoplophora glabripennis to male-produced pheromone and plant volatiles.
Chemical composition and antibacterial activity of the essential oil of Monticalia andicola (Asteraceae) collected in Venezuela.
Chemical composition and antimicrobial and antioxidant activities of essential oils and various extracts of Juniperus phoenicea L. (Cupressacees).
Essential oil composition of two new species of Phebalium (Rutaceae) from north-eastern NSW, Australia.
Chemical composition and antimicrobial activity of Clausena indica (Dalz) Oliv. (Rutaceae) essential oil from Vietnam.
The volatile constituents analysis of Lallemantia iberica (M.B.) Fischer & Meyer from Iran.
Manuka oil and phoebe oil are attractive baits for Xyleborus glabratus (Coleoptera: Scolytinae), the vector of laurel wilt.
Bioactivity-guided fractionation and GC/MS fingerprinting of Angelica sinensis and Angelica archangelica root components for antifungal and mosquito deterrent activity.
Monoterpene and Phenolic Compound Concentrations in Water-Stressed Red Pine Inoculated with Sphaeropsis sapinea.
Influence of OH scavenger on the water effect on secondary organic aerosol formation from ozonolysis of limonene, Delta3-carene, and alpha-pinene.
Organosulfate formation in biogenic secondary organic aerosol.
Chemical composition and fungitoxic activity of essential oil of Thuja orientalis L. grown in the north-western Himalaya.
Characterization of steam volatiles in the essential oil of black currant buds and the antioxidant properties of different bud extracts.
The essential oil qualitative and quantitative composition in the needles of Pinus sylvestris L. growing along industrial transects.
Sensitivity of terpene emissions to drought and fertilization in terpene-storing Pinus halepensis and non-storing Quercus ilex.
Morphology of antennal sensilla auricillica and their detection of plant volatiles in the Herald moth, Scoliopteryx libatrix L. (Lepidoptera: Noctuidae).
Physical and chemical responses of Sitka spruce (Picea sitchensis) clones to colonization by Heterobasidion annosum as potential markers for relative host susceptibility.
The role of genetic and chemical variation of Pinus sylvestris seedlings in influencing slug herbivory.
Enantiomeric monoterpene emissions from natural and damaged Scots pine in a boreal coniferous forest measured using solid-phase microextraction and gas chromatography/mass spectrometry.
Response to host volatiles by native and introduced populations of Dendroctonus valens (Coleoptera: Curculionidae, Scolytinae) in North America and China.
[Analysis of volatile constituents in leaves of three cypress species by gas chromatography/mass spectrometry].
Antifungal activity of Juniperus essential oils against dermatophyte, Aspergillus and Candida strains.
Composition and antibacterial activity of Abies balsamea essential oil.
Metabolism of Delta(3)-carene by human cytochrome p450 enzymes: identification and characterization of two new metabolites.
Continuous real-time analysis of products from the reaction of some monoterpenes with ozone using atmospheric sampling glow discharge ionization coupled to a quadrupole ion trap mass spectrometer.
Volatile components from mango (Mangifera indica L.) cultivars.
An experimental comparison of a kinetic model for the reaction of alpha-pinene and Delta(3)-carene with ozone and nitrogen oxides.
Dermal exposure to monoterpenes during wood work.
Study of the carbonyl products of terpene/OH radical reactions: detection of the 2,4-DNPH derivatives by HPLC-MS.
Effect of storage on the essential oil composition of Piper nigrum L. fruits of different ripening states.
Antioxidative properties of the essential oil from Pinus mugo.
Composition and antimicrobial properties of Sardinian Juniperus essential oils against foodborne pathogens and spoilage microorganisms.
Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth.
Respiratory symptoms and occupational exposures in New Zealand plywood mill workers.
Chemical composition of the essential oils of Juniperus from ripe and unripe berries and leaves and their antimicrobial activity.
Volatile constituents of the fruit and leaf oils of Thuja orientalis L. grown in Iran.
Exposure assessment to alpha- and beta-pinene, delta(3)-carene and wood dust in industrial production of wood pellets.
Antifungal activity of the essential oils from some species of the genus Pinus.
Age and space distributions of monoterpenes in fresh needles of Picea abies (L) Karst. Determined by gas chromatography-mass spectrometry.
Identification of volatile constituents of Tambourissa leptophylla.
Intraspecific chemical variability of the leaf essential oil of Juniperus phoenicea subsp. turbinata from Corsica.
Essential oil of Lepechinia schiedeana (Lamiaceae) from Costa Rica.
Sensory properties of selected terpenes. Thresholds for odor, nasal pungency, nasal localization, and eye irritation.
Differential Inhibition of Sphaeropsis sapinea Morphotypes by a Phenolic Compound and Several Monoterpenes of Red Pine.
Genetic determinism of δ3-carene in maritime pine using RAPD markers.
Transient re-emergence of oil of turpentine allergy in the pottery industry.
Semiochemicals from bark beetles: New results, remarks, and reflections.
Chiral specificity in responses by the bark beetleDendroctonus valens to host kairomones.
Influence of monoterpene vapors on spruce spider mite,Oligonychus ununguis, adult females.
Identification of cis- and trans-verbenol in human urine after occupational exposure to terpenes.
Pharmacological activity of the essential oil of Bupleurum gibraltaricum: anti-inflammatory activity and effects on isolated rat uteri.
Electroantennogram responses by mountain pine beetles,Dendroctonus ponderosae Hopkins, exposed to selected semiochemicals.
Effect of various essential oils isolated from Douglas fir needles upon sheep and deer rumen microbial activity.
[Hydroboration of (+)delta-3-carene].
[NEW PHARMACOLOGICAL PROPERTIES OF DELTA-3-CARENE. ANTIBACTERIAL AND EXPECTORANT EFFECTS].
Publications by J-Stage
Distillation Time Modifies Essential Oil Yield, Composition, and Antioxidant Capacity of Fennel (Foeniculum vulgare Mill)
Quantitative Evaluation of (+)-?3-Carene Metabolites from Living Larvae of Spodoptera litura by Headspace Solid-phase Microextraction

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
KEGG (GenomeNet):C09839
HMDB (The Human Metabolome Database):HMDB35619
Export Tariff Code:2902.19.0050
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 136.23751831055
Specific gravity @ 25 °C
Pounds per Gallon 7.156 to 7.223
Refractive Index 1.472 to 1.473 @ 20 °C
Melting Point 23 to 24°C @ 760 mm Hg
Boiling Point 169 to 174°C @ 705 mm Hg
Vapor Pressure 3.72 mmHg @ 25 °C
Flash Point TCC Value 46.11 °C TCC
logP (o/w) 4.38
Shelf life 12 months (or longer if stored properly.)
Storage notes Store under nitrogen.
Solubility
alcohol Yes
water, 4.581 mg/L @ 25 °C (est) Yes
organic solvents Yes
water No
Stability
alkali Unspecified

Organoleptic Properties

Odor Type: Citrus
citrus, terpenic, herbal, pine, solvent, resinous, phenolic, cypress, medicinal, woody
Odor strength medium
Substantivity < 1 hour(s) at 100.00 %
Luebke, William tgsc, (2017) At 100.00 %. citrus terpenic herbal pine solvent resinous phenolic cypress medicinal woody
Flavor Type: Citrus
citrus, pine, terpenic, herbal, resinous, tropical, peppery, juniper, wasabi
Luebke, William tgsc, (2017) Citrus pine terpenic herbal resinous tropical peppery juniper wasabi

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi N - Irritant, Dangerous for the environment.
R 10 - Flammable.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
R 38 - Irritating to skin.
R 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
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.
Oral/Parenteral Toxicity:
oral-rat LD50 [sex: M] 4800 mg/kg
Identity of compound not stated
(Moreno, 1972l)

oral-rat LD50 > 5000 mg/kg
Mixture of isomers. Only one dose tested
(Keating, 1972a)

oral-rat LD50 4800 mg/kg
Food and Cosmetics Toxicology. Vol. 11, Pg. 1053, 1973.

Dermal Toxicity:
Not determined
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 delta-3-carene usage levels up to:
1.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 290.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 40.00 (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: 18
Click here to view publication 18
average usual ppmaverage maximum ppm
baked goods: 10.0000050.00000
beverages(nonalcoholic): 15.0000050.00000
beverages(alcoholic): 20.0000060.00000
breakfast cereal: 10.0000050.00000
cheese: 1.000005.00000
chewing gum: 60.00000100.00000
condiments / relishes: 10.0000050.00000
confectionery froastings: 20.0000060.00000
egg products: --
fats / oils: 5.0000030.00000
fish products: 1.000005.00000
frozen dairy: 20.0000050.00000
fruit ices: 20.0000050.00000
gelatins / puddings: 5.0000040.00000
granulated sugar: --
gravies: 5.0000020.00000
hard candy: 40.0000080.00000
imitation dairy: 1.000005.00000
instant coffee / tea: 5.0000020.00000
jams / jellies: 5.0000040.00000
meat products: 1.000005.00000
milk products: 20.0000060.00000
nut products: 5.0000020.00000
other grains: 10.0000050.00000
poultry: 1.000005.00000
processed fruits: 5.0000020.00000
processed vegetables: 5.0000020.00000
reconstituted vegetables: 5.0000020.00000
seasonings / flavors: 10.0000050.00000
snack foods: 5.0000030.00000
soft candy: 20.0000060.00000
soups: 5.0000020.00000
sugar substitutes: 1.0000010.00000
sweet sauces: 15.0000050.00000

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 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

Statement on List of Representative Substances for Testing. The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000).
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

Safety and efficacy of eight compounds belonging to chemical group 31 (aliphatic and aromatic hydrocarbons) when used as flavourings for all animal species and categories
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):13466-78-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :26049
National Institute of Allergy and Infectious Diseases:Data
SCCNFP:opinion
WGK Germany:2
3,7,7-trimethylbicyclo[4.1.0]hept-3-ene
Chemidplus:0013466789
EPA/NOAA CAMEO:hazardous materials
RTECS:FH8400000 for cas# 13466-78-9