3-Carene

3-Carene
Names
	IUPAC names 3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene ; Car-3-ene
	Other names Δ3-Carene
Identifiers
CAS Number	13466-78-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1902767
ChEBI	CHEBI:7;
ChEMBL	ChEMBL506854 ;
ChemSpider	10660720 ;
ECHA InfoCard	100.033.367
EC Number	236-719-3;
Gmelin Reference	663435
KEGG	C11382 ;
PubChem CID	26049;
UNII	H2M15SNR6N ;
UN number	2319
CompTox Dashboard (EPA)	DTXSID4047462 ;
	InChI InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3 Key: KALFVDDBBPRATR-UHFFFAOYSA-N ; InChI=1/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3 Key: KALFVDDBBPRATR-UHFFFAOYAY;
	SMILES CC2(C)C\1CCC(C)/C=C/12;
Properties
Chemical formula	C10H16
Molar mass	136.238 g·mol−1
Density	0.86 g/cm3 (20 °C)[1]
Boiling point	170–172 °C (338–342 °F; 443–445 K)[1]
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H304, H315, H317, H412
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+310, P302+352, P303+361+353, P321, P331, P332+313, P333+313, P362, P363, P370+378, P403+235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

3-Carene is a bicyclic monoterpene consisting of fused cyclohexene and cyclopropane rings. It occurs as a constituent of turpentine,[2] with a content as high as 42% depending on the source. Carene has a sweet and pungent odor,[3] best described as fir needles, musky earth, and damp woodlands combination.[4]

A colorless liquid, it is not soluble in water, but miscible with fats and oils.[3] It is chiral, occurring naturally both as the racemate and enantio-enriched forms.

Reactions and uses

Treatment with peracetic acid gives 3,4-caranediol. Pyrolysis over ferric oxide induces rearrangement, giving p-cymene. Carene is used in the perfume industry and as a chemical intermediate.[2]

Because carene can be found in cannabis naturally, it can also be found in cannabis distillates. Greater concentrations of carene in a distillate give it an earthier taste and smell.[5]

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References

Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
M. Eggersdorfer (2005). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205.
Merck Index (12th ed.). 1996. p. 300. 1885.
Mediavilla, Vito, Simon Steinemann, Essential oil of Cannabis sativa L. strains. Journal of the International Hemp Association, 1997, 4(2):80-82.
"What is Delta 3 Carene?". ionizationlabs.com. Ionization Labs. Retrieved 6 August 2020.

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[GESTIS-1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[UllmannEgg-2] M. Eggersdorfer (2005). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205.

[Merck-3] Merck Index (12th ed.). 1996. p. 300. 1885.

[4] Mediavilla, Vito, Simon Steinemann, Essential oil of Cannabis sativa L. strains. Journal of the International Hemp Association, 1997, 4(2):80-82.

[5] "What is Delta 3 Carene?". ionizationlabs.com. Ionization Labs. Retrieved 6 August 2020.