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3-Carene

From Wikipedia, the free encyclopedia
(Redirected fromCarene)
"Carene" redirects here. For the town of ancient Mysia, seeCarene (Mysia).
3-Carene
Carene
Carene
Names
Preferred IUPAC name
3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
Other names
Δ3-Carene
Car-3-ene
Identifiers
3D model (JSmol)
1902767
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.033.367Edit this at Wikidata
EC Number
  • 236-719-3
663435
KEGG
UNII
UN number2319
  • InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3 checkY
    Key: KALFVDDBBPRATR-UHFFFAOYSA-N checkY
  • InChI=1/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h6-8H,4-5H2,1-3H3
    Key: KALFVDDBBPRATR-UHFFFAOYAY
  • CC1=CCC2C(C1)C2(C)C
Properties
C10H16
Molar mass136.238 g·mol−1
Density0.86 g/cm3 (20 °C)[1]
Boiling point170–172 °C (338–342 °F; 443–445 K)[1]
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H226,H304,H315,H317,H412
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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

3-Carene is a bicyclicmonoterpene consisting of fusedcyclohexene andcyclopropane rings. It occurs as a constituent ofturpentine,[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 offir 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 theracemate and enantio-enriched forms.

Reactions and uses

[edit]

Treatment withperacetic acid gives 3,4-caranediol.Pyrolysis overferric oxide induces rearrangement, givingp-cymene. Carene is used in theperfume industry and as a chemical intermediate.[2]

Because carene can be found incannabis 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 inmango, giving the fruit a characteristicpine-like flavor and aroma.

References

[edit]
  1. ^abRecord in theGESTIS Substance Database of theInstitute for Occupational Safety and Health
  2. ^abM. Eggersdorfer (2005). "Terpenes".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a26_205.ISBN 978-3-527-30673-2.
  3. ^abMerck 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. Retrieved6 August 2020.
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