Showing Compound 3,5,8-Megastigmatrien-7-one (FDB015480)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:52 UTC

Update date

2019-11-26 03:11:39 UTC

Primary ID

FDB015480

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3,5,8-Megastigmatrien-7-one

Description

beta-Damascenone, also known as damascenone, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, beta-damascenone is considered to be an isoprenoid lipid molecule. beta-Damascenone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. beta-Damascenone is a sweet, apple, and apple.rose tasting compound. beta-Damascenone has been detected, but not quantified in, several different foods, such as star fruits, sweet basils, garden tomato (var.), lemon balms, and cauliflowers. This could make beta-damascenone a potential biomarker for the consumption of these foods.

CAS Number

23726-93-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one	ChEBI
(e)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one	ChEBI
(e)-beta-Damascenone	ChEBI
beta-(e)-Damascenone	ChEBI
Damascenone	ChEBI
trans-beta-Damascenone	ChEBI
trans-Damascenone	ChEBI
(e)-b-Damascenone	Generator
(e)-Β-damascenone	Generator
b-(e)-Damascenone	Generator
Β-(e)-damascenone	Generator
trans-b-Damascenone	Generator
trans-Β-damascenone	Generator
b-Damascenone	Generator
Β-damascenone	Generator
1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one	HMDB
(2e)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one	ChEBI
(e)-β-damascenone	biospider
(e)-beta -Damascenone	HMDB
(e)-β-damascenone	Generator
β-(e)-damascenone	biospider
β-damascenone	biospider
2-Buten-1-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-	biospider
2,6,6-Trimethyl-1-trans-crotonoyl-1,3-cyclohexadiene	biospider
4-(2,6,6-Trimethylcyclohexa-1,3-dienyl)but-2-en-4-one	biospider
beta -(e)-Damascenone	HMDB
beta -Damascenone	HMDB
beta-Damascenone	biospider
Damascenone, trans-	biospider
Trans-β-damascenone	biospider
trans-beta -Damascenone	HMDB
trans-β-damascenone	Generator
β-(e)-damascenone	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	4.02	ALOGPS
logP	3.68	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.02 m³·mol⁻¹	ChemAxon
Polarizability	22.61 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	Yes	ChemAxon

Chemical Formula

C13H18O

IUPAC name

(2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one

InChI Identifier

InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+

InChI Key

POIARNZEYGURDG-FNORWQNLSA-N

Isomeric SMILES

C\C=C\C(=O)C1=C(C)C=CCC1(C)C

Average Molecular Weight

190.286

Monoisotopic Molecular Weight

190.1357652

Classification

Description

belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

enone (CHEBI:67251 )
apo carotenoid monoterpenoid (CHEBI:67251 )
cyclic monoterpene ketone (CHEBI:67251 )
C40 isoprenoids (tetraterpenes) (LMPR01070304 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 82.06%; H 9.53%; O 8.41%	DFC
Melting Point	Not Available
Boiling Point	Bp13 116-118°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01dm-5900000000-4bcd624fdf9c5e42b887	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1900000000-8da6e151fea92abe412a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kg-6900000000-2069d91b82e6511da0ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9200000000-6695f41d1b443f4da598	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-3f94da9b260ed91041b8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2900000000-7afc8b9366085d67da73	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007n-4900000000-d38de494cceadf7b6a17	JSpectraViewer

External Links

ChemSpider ID

4517997

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5366074

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36572

CRC / DFC (Dictionary of Food Compounds) ID

KCQ14-A:KCQ14-A

EAFUS ID

3741

Dr. Duke ID

DAMASCENONE|BETA-DAMASCENONE

BIGG ID

Not Available

KNApSAcK ID

C00035536

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

23726-93-4

GoodScent ID

rw1441071

SuperScent ID

5366074

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti edemic			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
rose	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 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
honey	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apple	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 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
smoky	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
tobacco	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apple.rose	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