Showing Compound alpha-Humulene (FDB015360)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:48 UTC

Update date

2020-09-17 15:30:33 UTC

Primary ID

FDB015360

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

alpha-Humulene

Description

alpha-humulene also known as Humulene or alpha-caryophyllene is a volatile organic compound that belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP; PMID:23746261) pathway in the cytoplasm. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Humulene is is a pale yellowish green clear liquid, soluble in alcohol that is barely soluble in water. It has a woody odor and adds a woody, oceanic-watery, spicy-clove note to perfumes ( http://www.thegoodscentscompany.com/data/rw1027221.html#tooccur). It contributes to the taste of the spice Persicaria odorata or Vietnamese coriander. Humulene is found in hops (Humulus lupulus; doi:10.1055/s-2006-962205), from which its name was derived. It is often found together with its isomer beta-caryophyllene in many other aromatic plants such pine trees ( PMID: 17396639), orange trees, marsh elders, tobacco, sunflowers, Salvia officinalis (common sage, culinary sage), Lindera strychnifolia Uyaku (Japanese spicebush, ginseng species and the Zingiberaceae (the ginger family). alpha-humulene, a very reactive volatile organic compound emitted by many organic plants, quickly combines with ozone in sunlight (photooxidation) to create secondary organic aerosols ( oi:10.1039/c0cp02379e). alpha-humulene has antibacterial and anti-biofilm properties against Bacteroides fragilis (PMID: 32073898) and demonstrated anti-inflammatory properties in an ovalbumin-induced model of airway allergic inflammation (PMID: 19438512).

CAS Number

6753-98-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(1E,4E,8E)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene	HMDB
(1E,4E,8E)-2,6,6,9-tetramethyl-1,4,8-cycloundecatriene	biospider
(1E,4E,8E)-2,6,6,9-Tetramethylcycloundeca-1,4,8-triene	HMDB
(1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene	biospider
(1E,4E,8E)-alpha-Humulene	HMDB
(1E,4E,8E)-alpha-humulene	biospider
(1E,4E,8E)-Humula-1(11),4,8-triene	HMDB
(1E,4E,8E)-humula-1(11),4,8-triene	biospider
(e,e,e)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene	HMDB
(E,E,E)-2,6,6,9-tetramethyl-1,4,8-cycloundecatriene	biospider

Showing 1 to 10 of 36 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	6.07	ALOGPS
logP	4.88	ChemAxon
logS	-4.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.55 m³·mol⁻¹	ChemAxon
Polarizability	26.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H24

IUPAC name

(1Z,4Z,8Z)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene

InChI Identifier

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-

InChI Key

FAMPSKZZVDUYOS-KXWHQPPKSA-N

Isomeric SMILES

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

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

Classification

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Humulane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Subcellular:

Biofluid and excreta:

Feces

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Pharmaceutical industry:

Anti-inflammatory

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp10 123°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 88.16%; H 11.84%	DFC
Melting Point	< 25 oC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	alpha-Humulene, non-derivatized, GC-MS Spectrum	splash10-0006-9300000000-96e2ddad1a99d808b4dd	Spectrum
Predicted GC-MS	alpha-Humulene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-0920000000-3e5845e9275b1b3231fa	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-d1375940e9b7ed7922b4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2930000000-cdb29a58477970796a70	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kr-4900000000-788e8bfc0021846819ae	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-8ecbabe7146ad2762752	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0390000000-984bd28446d79854bd71	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ri-1900000000-139cbaab33ea7f90de6c	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0079-0920000000-90d0407fa9aa4598cee3	2021-10-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-c084f3d998cc56a199d6	2021-10-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0190000000-0612dd5822c06422c9bb	2021-10-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-0900000000-358d2a7dc14a6841b1df	2021-10-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

5006149

ChEMBL ID

Not Available

KEGG Compound ID

C09684

Pubchem Compound ID

6508206

Pubchem Substance ID

Not Available

ChEBI ID

5768

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36467

CRC / DFC (Dictionary of Food Compounds) ID

JZV54-F:JZV54-F

EAFUS ID

Not Available

Dr. Duke ID

ALPHA-CARYOPHYLLENE|ALPHA-HUMULENE|HUMULENE

BIGG ID

Not Available

KNApSAcK ID

C00003147

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

6753-98-6

GoodScent ID

rw1027221

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti malarial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti plasmodial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Showing 1 to 4 of 4 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
wood	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 2 of 2 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.