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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24
Molecular Weight 204.3511
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HUMULENE

SMILES

C\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC1

InChI

InChIKey=FAMPSKZZVDUYOS-HRGUGZIWSA-N
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+

HIDE SMILES / InChI

Molecular Formula C15H24
Molecular Weight 204.3511
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Humulene (also known as α-caryophyllene, α-Humulene) is a ring-opened isomer of β-caryophyllene, with powerful anti-inflammatory activity equal to dexamethasone in an animal model. α-Humulene has been found in many aromatic plants on all continents, often together with its isomer β-caryophyllene. Proven α-humulene emitters into the atmosphere are pine trees, orange orchards, marsh elders, tobacco, and sunflower fields. Humulene possesses both topical and systemic anti-inflammatory properties and is an effective analgesic when taken topically, orally, or by aerosol. Humulene can produce ROS, leading to an antineoplastic effect by inducing apoptosis; although at moderate levels, ROS can increase tumor growth. β-Caryophyllene was synergistic with humulene in one study. Interestingly, humulene was shown to increase secretion of IL-8, a chemokine with various functions, including promoting angiogenesis, helpful in wound healing but not typically associated with anticancer compounds.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Mice, p.o. 50 mg/kg/day
Route of Administration: Other
In Vitro Use Guide
Antimycobacterial activity was assessed against Mycobacterium tuberculosis H37Ra using the microplate Alamar Blue assay (MABA). MIC for Humulene = 6.25mg/mL
Substance Class Chemical
Record UNII
54W56MD2WD
Record Status Validated (UNII)
Record Version