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;
ChEMBL	ChEMBL506854 ;
ChemSpider	10660720 ;
ECHA InfoCard	100.033.367
KEGG	C11382 ;
PubChem CID	26049;
UNII	H2M15SNR6N ;
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]
	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]

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.CS1 maint: uses authors parameter (link)
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.

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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.CS1 maint: uses authors parameter (link)

[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.