Xanthoxylin (CED0014224)

Record Information

Version

1.0

Creation Date

2016-05-25 20:58:55 UTC

Update Date

2026-08-17 23:54:46 UTC

Accession Number

CHEM023333

Identification

Common Name

Xanthoxylin

Class

Small Molecule

Description

Xanthoxylin is an organic compound with the chemical formula C10H12O4 and an average molecular weight of 196.20 g/mol. Xanthoxylin belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. This compound has been identified in three recorded sources. It is found in food, food processing, and cookware, specifically during the preparation of wort and fermentation processes for beer. Additionally, it is present in indoor air, dust, and atmospheric transport. The recorded route of exposure for this substance is inhalation.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Hydroxy-4,6-dimethoxyacetophenone	MeSH
Brevifolin	MeSH
Xanthoxyline	MeSH
1-(2-Hydroxy-4,6-dimethoxyphenyl)-ethanone	HMDB
1-(2-Hydroxy-4,6-dimethoxyphenyl)ethan-1-one	HMDB
1-(2-Hydroxy-4,6-dimethoxyphenyl)ethanone	HMDB
1-Acetyl-2-hydroxy-4,6-dimethoxybenzene	HMDB
2'-Hydroxy-4',6'-dimethoxy-acetophenone	HMDB
2'-Hydroxy-4',6'-dimethoxyacetophenone	HMDB
2,4-Di-O-methylphloroacetophenone	HMDB
2-Hydroxy-4, 6-dimethoxyacetophenone	HMDB
2-Hydroxyl-4,6-dimethoxy-acetophenone	HMDB
4, 6-Dimethoxy-2-hydroxyacetophenone	HMDB
4,6-Dimethoxy-2-hydroxyacetophenone	HMDB
6-Methoxypaeonol	HMDB
Acetophenone der.	HMDB
Acetophenone, 2'-hydroxy-4',6'-dimethoxy- (8ci)	HMDB
Brevifolin (zanthoxylum)	HMDB
Phloracetophenone dimethyl ether	HMDB
Phloroacetophenone 2,4-dimethyl ether	HMDB

Chemical Formula

C₁₀H₁₂O₄

Average Molecular Mass

196.200 g/mol

Monoisotopic Mass

196.074 g/mol

CAS Registry Number

90-24-4

IUPAC Name

1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one

Traditional Name

xanthoxylin

SMILES

COC1=CC(O)=C(C(C)=O)C(OC)=C1

InChI Identifier

InChI=1S/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3

InChI Key

FBUBVLUPUDBFME-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Acetophenone
Phenoxy compound
Anisole
Benzoyl
Phenol ether
Aryl alkyl ketone
Methoxybenzene
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ether
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carboxylic ester (CHEBI:10070 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.46 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.56	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.37 m³·mol⁻¹	ChemAxon
Polarizability	19.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-001i-2900000000-7f4577d7995fbddd577f	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-001i-0900000000-3cd64b53df7c93b840ad	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-001i-2900000000-7f4577d7995fbddd577f	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-001i-0900000000-3cd64b53df7c93b840ad	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001i-2900000000-7f3dc4cd71234f173a0c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0uk9-7490000000-7f3ba8e004b9854018cb	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-1497100000-bce3b539553244813746	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gba-3900000000-3016175ddc355d5ca94e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01p9-0900000000-43bfa0bde3b4f442ecdc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-22166f1027bf3e06de04	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-568f7cd67cd1fc802fd4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0lk9-0900000000-5a2b415f82cac4381e39	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002b-0900000000-a965b10d2d3aad048c6e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ufr-0900000000-4f70cdfc7d4f2a990f84	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-db6a23774c46b4a95353	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-ef5b20a480a33ea141b9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-2900000000-2de8c0fec8d00685e7f7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-41dccc88b05c10fc0199	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udj-1900000000-942e591bf3dc0f2bb351	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0592-6900000000-a42426d4ccaaf03e24ee	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-43e8b5890016d7697537	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002b-0900000000-58ec00da7265801de99e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001u-9500000000-39958fd208cc560c3c1f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-3fa6590d885bd1307480	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0900000000-7338902de2bb9e734714	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06ec-9400000000-59b2e65e6acc03f454ae	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2798.0	Log mg/kg	[1600:5000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
19	Indoor air	Air, dust & atmospheric transport	Not Available
544	Fermentation Processes For Beer	Food, food processing & cookware	Not Available
550	Preparation Of Wort	Food, food processing & cookware	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 1B1	Q16678	Humans	Predicted (SEA)	24.9118
Click to view 3D structure	Cytochrome P450 1A1	P04798	Humans	Predicted (SEA)	18.9952
Click to view 3D structure	Polyunsaturated fatty acid 5-lipoxygenase	P09917	Humans	Predicted (SEA)	38.9246
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	157.333
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	136.392
Click to view 3D structure	Transthyretin	P02766	Humans	Predicted (SEA)	12.378
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	58.3091
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	142.308
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	87.9696
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	127.361
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	273.251
Click to view 3D structure	Broad substrate specificity ATP-binding cassette transporter ABCG2	Q9UNQ0	Humans	Predicted (SEA)	93.3412
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	81.5081
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	341.914
Click to view 3D structure	Transient receptor potential cation channel subfamily V member 1	Q8NER1	Humans	Predicted (SEA)	49.045
Click to view 3D structure	Nuclear factor erythroid 2-related factor 2	Q16236	Humans	Predicted (SEA)	13.5458
Click to view 3D structure	Transient receptor potential cation channel subfamily A member 1	Q6RI86	Rattus norvegicus	Predicted (SEA)	11.2103
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	53.0932
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	66.9503
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	71.6991
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	204.276
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	107.977
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	143.943
Click to view 3D structure	Transcription factor p65	Q04207	Mus musculus	Predicted (SEA)	7.47353
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Predicted (SEA)	137.871