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Humulene information


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
CAS Number
  • 6753-98-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:5768 checkY
ChEMBL
  • ChEMBL251280 checkY
ChemSpider
  • 4444853 checkY
ECHA InfoCard 100.027.106 Edit this at Wikidata
PubChem CID
  • 5281520
UNII
  • 54W56MD2WD checkY
CompTox Dashboard (EPA)
  • DTXSID30858793 Edit this at Wikidata
InChI
  • 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
SMILES
  • C\1=C/C(C)(C)C/C=C(/CC/C=C(/C/1)C)C
Properties[1]
Chemical formula
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):
LD50 (median dose)
>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 ?)
Infobox references

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.[2] Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

  1. ^ Merck Index, 12th Edition, 4789
  2. ^ Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. <http://realbeer.com/hops/aroma.html> Accessed July 21, 2010

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Humulene

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Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting...

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Hops

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hydrocarbons consisting of myrcene, humulene and caryophyllene. Myrcene is responsible for the pungent smell of fresh hops. Humulene and its oxidative reaction...

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Zerumbone synthase

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name 10-hydroxy-alpha-humulene:NAD+ oxidoreductase. This enzyme catalyses the following chemical reaction 10-hydroxy-alpha-humulene + NAD+ ⇌ {\displaystyle...

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Kumquat

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sesquiterpenes such as α-bergamotene (0.021%), caryophyllene (0.18%), α-humulene (0.07%) and α-muurolene (0.06%), and these contribute to the spicy and...

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Cannabis sativa

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Linalool Limonene Trans-β-ocimene α-Terpinolene Trans-caryophyllene α-Humulene, contributes to the characteristic aroma of Cannabis sativa Caryophyllene...

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Caryophyllene

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as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is...

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Cardamom

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(up to 70%) plus β-pinene (16%); furthermore, α-pinene, α-terpineol and humulene are found. In 2022, world production of cardamom (included with nutmeg...

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Cascade hop

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the US variety. The Tasmanian variety contains less myrcene oil and more humulene oil as well as other smaller differences. A variety of Cascade is also...

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Oil of clove

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consists of 70–82% eugenol, and some amounts of beta Caryophyllene and alpha Humulene. Stem oil is derived from the twigs of S. aromaticum. It consists of 85–92%...

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Terpene

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aroma and flavor of hops comes, in part, from sesquiterpenes (mainly α-humulene and β-caryophyllene), which affect beer quality. Some form hydroperoxides...

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Scutellaria lateriflora

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lateriflora contains τ-cadinene, calamenene, β-elemene, α-cubebene, and α-humulene.[citation needed] Its extracts are used in herbal medicine intended as...

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Eleutherococcus senticosus

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(26%), β-caryophyllene (7%), germacrene D (7%), β-bisabolene (5%), and α-humulene (4%). Extracts from the root of Eleutherococcus senticosus, including eleutherosides...

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Sesquiterpene

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end of the chain to the other end can lead to macrocyclic rings such as humulene. The cadinenes contain two fused six-membered rings. Caryophyllene, a component...

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Chrysopogon zizanioides

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terpinen-4-ol 5-epiprezizane khusimene α-muurolene khusimone Calacorene β-humulene α-longipinene γ-selinene δ-selinene δ-cadinene valencene calarene,-gurjunene...

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Coleus amboinicus

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essential oil of Coleus amboinicus are carvacrol (28.65%), thymol (21.66%), α-humulene (9.67%), undecanal (8.29%), γ-terpinene (7.76%), p-cymene (6.46%), caryophyllene...

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Saaz hops

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(as % of total oils) 0.4–0.8 N/A Caryophyllene (as % of total oils) 6–9 7 Humulene (as % of total oils) 15–25 23 Farnesene (as % of total oils) 14–20 N/A...

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Persicaria odorata

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the alcohols dodecanol (44%) and decanol (11%). Sesquiterpenes such as α-humulene and β-caryophyllene comprise about 15% of its oil. C-Methylated homoisoflavanones...

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Lavender oil

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Sesquiterpenes β-Caryophyllene 4.62% 2.10% β-Farnesene 2.73% Germacrene 0.27% α-Humulene 0.28% Ketones Camphor 0.85% 13.00 % 3-Octanone 0.72% Cryptone 0.35%...

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Secondary metabolite

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Structural formula for humulene, a monocyclic sesquiterpene (called so because it contains 15 carbon atoms) that is built from three C5 units derived from...

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Beer

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8-prenylnaringenin which is a potent phytoestrogen. Hop also contains myrcene, humulene, xanthohumol, isoxanthohumol, myrcenol, linalool, tannins, and resin. The...

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Cannabis flower essential oil

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α-terpinolene (7.0–16.6 %), trans-caryophyllene (12.2.–18.9 %), and α-humulene (6.1–8.7 %). The main differences between the cultivars were found in the...

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Humulus lupulus

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provide stability and allow it to climb. H. lupulus contains myrcene, humulene, xanthohumol, myrcenol, linalool, tannins, and resin. Hops are unique for...

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C15H24

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g/mol) may refer to: Farnesene Bergamotene Bisabolene Elemene Germacrene Humulene Zingiberene Amorpha-4,11-diene Aristolochene Cadinene Caryophyllene Guaiene...

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Hydrocotyle sibthorpioides

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stigmasterol, stigmasterol isomers, trans-β-farnesene, udosaponin B, α-humulene, α-pinene, β-caryophyllene, and β-pinene. Other compounds identified by...

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Tordylium apulum

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(17.3), α-humulene (11.4%) and octyl octanoate (8.8%). Essential oil from aerial parts of T. apulum from Greece was reported to have α-humulene (28.7%)...

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