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Showing Compound Herniarin (FDB000963)

Record Information
Version1.0
Creation date2010-04-08 22:04:47 UTC
Update date2025-11-18 22:26:47 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
MOLSDFPDBSMILESInChI
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-2.6ALOGPS
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
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-3900000000-17e44e05c8fe2491778a2015-03-01View Spectrum
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
Predicted GC-MSHerniarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00e9-0900000000-4a3dcfd5346e0e2a65ca2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00e9-0900000000-e8134a5ce939ed3891102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00e9-0900000000-e8134a5ce939ed3891102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00b9-2900000000-8975e7f06b2c1779fc872017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 12V, negativesplash10-03dl-5900000000-d235a93122ae0924491c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 15V, negativesplash10-03ec-7900000000-a0be9b4582f5680772392020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 22V, negativesplash10-03ec-9800000000-fb88eaf46b524a0103672020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-001i-4900000000-79f400e005b4b0abd2202020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-000l-9800000000-defb1852c01d2e5c38732020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-0006-9600000000-0b4321e67197e681a6c62020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-8662befff7041bc3c0192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9600000000-c8338c49921cebe4c8082021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-5900000000-7d4b5b1155355c18e6802021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-a780bc6bc930a176af922021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-2a59cdf525e794c8bdd72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-6233a6992d4f3e8c7c6a2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-0b88e2f92a1ca7f4b51c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-9886d3e9db07e94c90082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fis-3900000000-e49193208460a6f4cf592016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-b25d33bd5abcda83159d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-bc4c58f50f3e417616c42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgi-2900000000-6b0a0a442b520d5079b62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-00ffe2c25b8beb0eeaa02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-3ab745d21b37980c43612021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-7900000000-5a569237127af07c25c12021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, CDCl3, experimental)Spectrum
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 IDHerniarin
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 agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
Anti-allergic50857 An agent that reduces or blocks allergic reactions, commonly used to manage symptoms of allergies, such as itching, sneezing, and inflammation, by inhibiting the release of histamine and other chemical mediators, providing relief in conditions like hay fever, asthma, and skin allergies.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.DUKE
CandidicideAn agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.DUKE
CholagogueAn agent that stimulates the release of bile from the gallbladder, promoting digestion and relieving bile duct issues. Therapeutically, it aids in treating gallstones, jaundice, and liver disorders, while also supporting digestive health.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
PhotoactiveA compound that responds to light, often used in photodynamic therapy to treat cancer and skin disorders, with applications in wound healing, antimicrobial treatments, and diagnostic imaging, by triggering chemical reactions upon exposure to sunlight or ultraviolet radiation.DUKE
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.