ChemFOnt: Showing chemical card for Apo-9-zeaxanthinone (CFc000333029)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:44 UTC

Chemfont ID

CFc000333029

Molecule Identification

Common Name

Apo-9-zeaxanthinone

Definition

Apo-9-zeaxanthinone is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Apo-9-zeaxanthinone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Apo-9-zeaxanthinone can be found in a number of food items such as red bell pepper, yellow bell pepper, green bell pepper, and pepper (c. annuum), which makes apo-9-zeaxanthinone a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-b-ionone	Generator
3-Hydroxy-β-ionone	Generator
(3E)-4-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one	HMDB
(3E)-4-[(4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-3-buten-2-one	HMDB
(3R)-3-Hydroxy-beta-ionone	HMDB
(3R)-3-Hydroxy-β-ionone	HMDB
(R)-(-)-3-Hydroxy-beta-ionone	HMDB
(R)-(-)-3-Hydroxy-β-ionone	HMDB
(R)-3-Hydroxy-beta-ionone	HMDB
(R)-3-Hydroxy-β-ionone	HMDB
3beta-Hydroxymegastigma-5,7-dien-9-one	HMDB
3Β-hydroxymegastigma-5,7-dien-9-one	HMDB
Apo-9-zeaxanthinone	HMDB
3-Hydroxy-beta-ionone	HMDB

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

(3E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one

Traditional Name

(3R)-hydroxy-β-ionone

CAS Registry Number

50281-38-4

SMILES

CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C

InChI Identifier

InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1

InChI Key

HFRZSVYKDDZRQY-MVIFTORASA-N

Chemical Taxonomy

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

Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

apo carotenoid monoterpenoid (CHEBI:53173 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0036821)

Food

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	2.1	ALOGPS
logP	1.89	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.49 m³·mol⁻¹	ChemAxon
Polarizability	24.05 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