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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:07 UTC
Update Date2022-03-07 02:53:32 UTC
HMDB IDHMDB0032989
Secondary Accession Numbers
  • HMDB32989
Metabolite Identification
Common Name4-Methylumbelliferyl acetate
Description4-Methylumbelliferyl acetate, also known as 4-methyl-7-acetyloxy coumarin or 7-acetoxy-4-methylchromen-2-one, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 4-Methylumbelliferyl acetate has been detected, but not quantified in, a few different foods, such as fenugreeks (Trigonella foenum-graecum), green vegetables, and herbs and spices. This could make 4-methylumbelliferyl acetate a potential biomarker for the consumption of these foods. 4-Methylumbelliferyl acetate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 4-Methylumbelliferyl acetate.
Structure
Thumb
Synonyms
ValueSource
4-Methyl-7-acetyloxy coumarinChEBI
7-(Acetyloxy)-4-methyl-2-benzopyroneChEBI
7-(Acetyloxy)-4-methyl-2H-1-benzopyran-2-oneChEBI
7-Acetoxy-4-methylchromen-2-oneChEBI
7-Acetoxy-4-methylcoumarinChEBI
beta-Methylumbelliferyl acetateChEBI
b-Methylumbelliferyl acetateGenerator
b-Methylumbelliferyl acetic acidGenerator
beta-Methylumbelliferyl acetic acidGenerator
Β-methylumbelliferyl acetateGenerator
Β-methylumbelliferyl acetic acidGenerator
4-Methylumbelliferyl acetic acidGenerator
7-Acetoxy-4-methyl-2H-1-benzopyran-2-oneHMDB
4-MUAMeSH, HMDB
7AMCMeSH, HMDB
Chemical FormulaC12H10O4
Average Molecular Weight218.2054
Monoisotopic Molecular Weight218.057908808
IUPAC Name4-methyl-2-oxo-2H-chromen-7-yl acetate
Traditional Name4-methylumbelliferyl acetate
CAS Registry Number2747-05-9
SMILES
CC(=O)OC1=CC=C2C(C)=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C12H10O4/c1-7-5-12(14)16-11-6-9(15-8(2)13)3-4-10(7)11/h3-6H,1-2H3
InChI KeyHXVZGASCDAGAPS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point153 - 154 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility355.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010978
KNApSAcK IDNot Available
Chemspider ID359
KEGG Compound IDC03837
BioCyc IDCPD-181
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound366
PDB IDNot Available
ChEBI ID17763
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1213691
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular weight:
68898.39
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:
ESD
Uniprot ID:
P10768
Molecular weight:
31462.545
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails