Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:04:47 UTC
Update date2020-09-17 15:34:38 UTC
Primary IDFDB000963
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHerniarin
Description7-Methoxycoumarin or Herniarin, also known as ayapanin is a methoxy derivative of coumarin or a methyl derivative of umbelliferone. It 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). 7-Methoxycoumarin is a neutral, hydrophobic molecule that is not soluble in water. It exists as a white to pale yellow powder. It has a pleasant balsamic, sweet or tonka taste/odor. 7-Methoxycoumarin is used as a scent or aroma agent in perfumes, lotions, facial moisturizers, hand creams, hair conditioners, household aerosols, lip balms and baby oils. 7-Methoxycoumarin occurs naturally in many plants and foods and has been detected, but not quantified in, several different plants, such as barley, tarragons, roman camomiles, fruits, and wild celeries. This could make 7-methoxycoumarin a potential biomarker for the consumption of these foods.
CAS Number531-59-9
Structure
Thumb
Synonyms
SynonymSource
7-Methoxy-2H-1-benzopyran-2-oneChEBI
7-MethoxycoumarinChEBI
AyapaninChEBI
HerniarineChEBI
MethylumbelliferoneChEBI
7-(Methyloxy)-2H-chromen-2-oneHMDB
7-Methoxy-2H-1-benzopyran-2-one, 9ciHMDB
7-Methoxy-2H-chromen-2-oneHMDB
7-Methoxy-coumarinHMDB
7-METHOXYCOURMARINHMDB
7-Methyl ether derivative OF umbelliferoneHMDB
Coumarin, 7-methoxy- (8ci)HMDB
Herniarin (6ci)HMDB
Methyl umbelliferyl etherHMDB
Umbelliferone methyl etherHMDB
2H-1-Benzopyran-2-one, 7-methoxy-biospider
7-(methyloxy)-2H-chromen-2-onebiospider
7-Methoxy-2H-1-benzopyran-2-one, 9CIdb_source
7-Methyl ether derivative of Umbelliferonebiospider
Coumarin, 7-methoxy-biospider
Coumarin, 7-methoxy- (8CI)biospider
Herniarindb_source
Herniarin (6CI)biospider
METHOXYCOURMARIN, 7-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP1.88ALOGPS
logP1.63ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.01 m³·mol⁻¹ChemAxon
Polarizability17.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H8O3
IUPAC name7-methoxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C10H8O3/c1-12-8-4-2-7-3-5-10(11)13-9(7)6-8/h2-6H,1H3
InChI KeyLIIALPBMIOVAHH-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C=CC(=O)O2)C=C1
Average Molecular Weight176.171
Monoisotopic Molecular Weight176.047344118
Classification
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
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.18%; H 4.58%; O 27.25%DFC
Melting PointMp 117-118°DFC
Boiling PointNot Available
Experimental Water Solubility0.133 mg/mLBEILSTEIN
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data320 (e 14125) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004j-3900000000-17e44e05c8fe2491778aSpectrum
GC-MSHerniarin, non-derivatized, GC-MS Spectrumsplash10-005a-5900000000-a51cb4413d70fe3ecdccSpectrum
GC-MSHerniarin, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5b9073b915d724268702Spectrum
GC-MSHerniarin, non-derivatized, GC-MS Spectrumsplash10-005a-5900000000-a51cb4413d70fe3ecdccSpectrum
GC-MSHerniarin, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5b9073b915d724268702Spectrum
Predicted GC-MSHerniarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-0900000000-213046cadb13b2437780Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00e9-0900000000-4a3dcfd5346e0e2a65caSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00e9-0900000000-e8134a5ce939ed389110Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00e9-0900000000-e8134a5ce939ed389110Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00b9-2900000000-8975e7f06b2c1779fc87Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 12V, negativesplash10-03dl-5900000000-d235a93122ae0924491cSpectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 15V, negativesplash10-03ec-7900000000-a0be9b4582f568077239Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 22V, negativesplash10-03ec-9800000000-fb88eaf46b524a010367Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-001i-4900000000-79f400e005b4b0abd220Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-000l-9800000000-defb1852c01d2e5c3873Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-0006-9600000000-0b4321e67197e681a6c6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-0b88e2f92a1ca7f4b51cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-9886d3e9db07e94c9008Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fis-3900000000-e49193208460a6f4cf59Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-b25d33bd5abcda83159dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-bc4c58f50f3e417616c4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgi-2900000000-6b0a0a442b520d5079b6Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID10295
ChEMBL IDCHEMBL49732
KEGG Compound IDC09268
Pubchem Compound ID10748
Pubchem Substance IDNot Available
ChEBI ID5679
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29758
CRC / DFC (Dictionary of Food Compounds) IDBSX04-T:BNX60-Y
EAFUS IDNot Available
Dr. Duke IDHERNIARIN
BIGG IDNot Available
KNApSAcK IDC00002476
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID531-59-9
GoodScent IDrw1031831
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
candidicideDUKE
cholagogueDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
photoactiveDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
balsamic
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tonka
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.