3-Carene

3-Carene
Names
	Preferred IUPAC name 3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
	Other names Δ3-Carene; Car-3-ene
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)
Boiling point	170–172 °C (338–342 °F; 443–445 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H304, H315, H317, H412
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301 P310, P302 P352, P303 P361 P353, P321, P331, P332 P313, P333 P313, P362, P363, P370 P378, P403 P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 a combination of fir needles, musky earth, and damp woodlands.^[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] 3-Carene is also present in mango, giving the fruit a characteristic pine-like flavor and aroma.

References

^ ^a ^b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ ^a ^b M. Eggersdorfer (2005). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.
^ ^a ^b 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.

[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. ISBN 978-3527306732.

[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.

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