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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24
Molecular Weight 204.3516
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HUMULENE

SMILES

C/C/1=C(/[H])\CC/C(=C(\[H])/CC(C)(C)/C(/[H])=C(\[H])/C1)/C

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 204.3516
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17845001 | https://www.ncbi.nlm.nih.gov/pubmed/17396639

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

Mice, p.o. 50 mg/kg/day
Route of Administration: Other
Antimycobacterial activity was assessed against Mycobacterium tuberculosis H37Ra using the microplate Alamar Blue assay (MABA). MIC for Humulene = 6.25mg/mL
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:46:17 UTC 2021
Edited
by admin
on Sat Jun 26 13:46:17 UTC 2021
Record UNII
54W56MD2WD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HUMULENE
MI  
Common Name English
HUMULENE, ALPHA-
Common Name English
1,4,8-CYCLOUNDECATRIENE, 2,6,6,9-TETRAMETHYL-, (1E,4E,8E)-
Systematic Name English
.ALPHA.-HUMULENE
Common Name English
(1E,4E,8E)-2,6,6,9-TETRAMETHYL-1,4,8-CYCLOUNDECATRIENE
Systematic Name English
.ALPHA.-CARYOPHYLLENE
Common Name English
HUMULENE [MI]
Common Name English
1,4,8-CYCLOUNDECATRIENE, 2,6,6,9-TETRAMETHYL-, (E,E,E)-
Systematic Name English
(+/-)-.ALPHA.-HUMULENE
Common Name English
Code System Code Type Description
MERCK INDEX
M6062
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
HUMULENE
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY
MESH
C042686
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY
RXCUI
2266811
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY
EPA CompTox
6753-98-6
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY
CAS
6753-98-6
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY
FDA UNII
54W56MD2WD
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY
PUBCHEM
5281520
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY
ECHA (EC/EINECS)
229-816-7
Created by admin on Sat Jun 26 13:46:17 UTC 2021 , Edited by admin on Sat Jun 26 13:46:17 UTC 2021
PRIMARY
Related Record Type Details
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Sesquiterpene Class