Showing Compound Xanthoxyletin (FDB012133)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:00 UTC

Update date

2019-11-26 03:06:15 UTC

Primary ID

FDB012133

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Xanthoxyletin

Description

Xanthoxyletin belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Xanthoxyletin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Xanthoxyletin has also been detected, but not quantified in, a few different foods, such as herbs and spices, lemons (Citrus limon), and mandarin orange (clementine, tangerine). This could make xanthoxyletin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xanthoxyletin.

CAS Number

84-99-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9ci	HMDB
5-Methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one	HMDB
Xanthoxylin N	HMDB
Xanthoxyloin	HMDB
Xanthoxyletin	MeSH
5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.53	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.41 m³·mol⁻¹	ChemAxon
Polarizability	26.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H14O4

IUPAC name

5-methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one

InChI Identifier

InChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11-9(14(10)17-3)4-5-13(16)18-11/h4-8H,1-3H3

InChI Key

JSJIIHRNDMLJGK-UHFFFAOYSA-N

Isomeric SMILES

COC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O2

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

Classification

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:69929 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 69.76%; H 5.46%; O 24.78%	DFC
Melting Point	Mp 133°	DFC
Boiling Point	Not Available
Experimental Water Solubility	cold water]
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	Xanthoxyletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-07ef-1190000000-78b72a1e70ea0b853ccc	Spectrum
Predicted GC-MS	Xanthoxyletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0uei-0940000000-f1e9eeeb83d8740504fc	Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0890000000-3a18d9c240e9f3626355	Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-056r-0290000000-1de65956796614ac099e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-aa6d574f073513b5a829	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-6c6860209ee19099b43c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gi0-4890000000-1ab1343a5be832f0b76e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-573b07a2c6c0cb5cbcd5	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-fb78f7d59b6f70625682	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ow-0980000000-b3f729731c4334112db9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-5899da0eda98839d58ad	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-2cf3ccdcea338c77fa5a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-1290000000-6d0938937a8c48a429ed	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-c2a50a42dfada53572a9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-0090000000-bb952c86674434372ddd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02ti-0290000000-4afb4baf58c4f7b7019a	Spectrum