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Humulene was the first terpene found in hops. Its aroma contains earthy, woody, and spicy notes. Besides cannabis, it can be also found in clove, sage, and black pepper. It has a variety of medical properties. Early research has shown humulene to be anti-proliferative, meaning it prevents cancer cells from growing. Also, it proved to be effective in suppressing appetite, making it a potential weight loss tool. Furthermore, like many other cannabis terpenes mentioned above, it also reduces inflammation, relieves pain, and fights bacterial infections.

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Humulene (Wikipedia)
Not to be confused with humulone.

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

Humulene
Humulene
Humulene
Names
IUPAC name
[1(11)E,4E,8E]-Humula-1(11),4,8-triene
Systematic IUPAC name
(1E,4E,8E)-2,6,6,9-Tetramethylcycloundeca-1,4-8-triene
Other names
alpha-Caryophyllene; 3,7,10-Humulatriene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.027.106 Edit this at Wikidata
UNII
  • InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6+,13-7+,14-10+ checkY
    Key: FAMPSKZZVDUYOS-HRGUGZIWSA-N checkY
  • InChI=1/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6+,13-7+,14-10+
    Key: FAMPSKZZVDUYOS-HRGUGZIWBF
  • C\1=C/C(C)(C)C/C=C(/CC/C=C(/C/1)C)C
Properties
C15H24
Molar mass 204.357 g·mol−1
Appearance Pale yellowish green clear liquid
Density 0.886 g/cm3
Melting point < 25 °C (77 °F; 298 K)
Boiling point 106 to 107 °C (223 to 225 °F; 379 to 380 K) at 5 mmHg
Hazards
Lethal dose or concentration (LD, LC):
>48 mg/kg
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Humulene (Wiktionary)

English

Noun

humulene (countable and uncountable, plural humulenes)

  1. A naturally-occurring monocyclic sesquiterpene found in the essential oils of Humulus lupulus (hops).

Related terms

  • humulone
 Read More
Caryophyllene, α-Humulene, α-Caryophyllene, Humulon, α-Humulon

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