AFCDB: Antheraxanthin (FDB014611)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:22 UTC

Update date

2019-11-26 03:10:27 UTC

Primary ID

FDB014611

Secondary Accession Numbers

FDB014598
FDB014193

Chemical Information

FooDB Name

Antheraxanthin

Description

Antheraxanthin a is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Antheraxanthin a is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Antheraxanthin a can be found in herbs and spices, which makes antheraxanthin a a potential biomarker for the consumption of this food product.

CAS Number

144-68-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00066 g/L	ALOGPS
logP	8.37	ALOGPS
logP	7.8	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193.64 m³·mol⁻¹	ChemAxon
Polarizability	73.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C40H56O3

IUPAC name

6-[(1E,3Z,5E,7E,9E,11Z,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

InChI Identifier

InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15-,30-16+,31-19+,32-20-

InChI Key

OFNSUWBAQRCHAV-SPHDKFQHSA-N

Isomeric SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)CC(O)CC1(C)C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/C12OC1(C)CC(O)CC2(C)C

Average Molecular Weight

584.8708

Monoisotopic Molecular Weight

584.422945658

Classification

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Oxepane
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 82.14%; H 9.65%; O 8.21%	DFC
Melting Point	Not Available
Boiling Point	Not Available
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

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Antheraxanthin B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-0000190000-7bd0e13d8f206a320dee	Spectrum
Predicted GC-MS	Antheraxanthin B, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-8000049000-5452827d88d2c1785b4b	Spectrum
Predicted GC-MS	Antheraxanthin B, "Antheraxanthin A,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Antheraxanthin B, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Antheraxanthin B, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Antheraxanthin B, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Antheraxanthin B, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Antheraxanthin B, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0111290000-ea6890da97668c034888	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0292-0896860000-8e1de2282adddce55f27	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2789110000-c41e5f7b6b437034be0b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-4896e855ba554115e448	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-0000090000-5884d599c1d784a6255d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00li-2700690000-3f9351aa3d43453e94db	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0100090000-eb4030a53043c4ed7051	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0103290000-06cee3361f8e19701d04	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-0229430000-377366a3cb24c383831f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0021290000-1af16436d5f9e5128cb3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0133390000-ac72fbcf22306f7a227f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-1349710000-37173bb77500fabdeb90	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

JSX21-G:JSX21-G

EAFUS ID

Not Available

Dr. Duke ID

ANTHERAXANTHIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
colorant	37958		DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

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).

Antheraxanthin (FDB014611)

Structure for FDB014611 (Antheraxanthin)