Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-15 04:56:50 UTC
NP-MRD IDNP0000005
Secondary Accession NumbersNone
Natural Product Identification
Common NameCoumarin
DescriptionCoumarin belongs to the class of chemicals known as chromenones. Specifically it is a chromenone having the keto group located at the 2-position. A chromenone is a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain forming a second six-membered heterocycle that shares two carbons with the benzene ring. Coumarin is also described as a benzopyrone and is considered as a lactone. Coumarin is a colorless crystalline solid with a bitter taste and sweet odor resembling the scent of vanilla or the scent of newly-mowed or recently cut hay. It is a chemical poison found in many plants where it may serve as a chemical defense against predators. Coumarin occurs naturally in many plants and foods such as the tonka bean, woodruff, bison grass, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, tobacco, wine, and other foodstuffs. Coumarin concentrations in these plants, spices, and foods range from <1 mg/kg in celery, to 7000 mg/kg in cinnamon, and up to 87,000 mg/kg in cassia. An estimate of human exposure to coumarin from the diet has been calculated to be 0.02 Mg/kg/day. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5% To 6.4% In fine fragrances to <0.01% In detergents. An estimate for systemic exposure of humans from the use of fragranced cosmetic products is 0.04 Mg/kg BW/day, assuming complete dermal penetration. The use of coumarin as a food additive was banned by the FDA in 1954 based on reports of hepatotoxicity in rats. It has clinical value as the precursor for several anticoagulants, notably warfarin. Coumarins, as a class, are comprised of numerous naturally occurring benzo-alpha-pyrone compounds with important and diverse physiological activities. Due to its potential hepatotoxic effects in humans, the European Commission restricted coumarin from naturals as a direct food additive to 2 mg/kg food/day, with exceptions granting higher levels for alcoholic beverages, caramel, chewing gum, and certain 'traditional foods'. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. Exposure ranges from 11 mg/day for consumption of natural food ingredients to 7 g/day following clinical administration. Although adverse effects in humans following coumarin exposure are rare, and only associated with clinical doses, recent evidence indicates coumarin causes liver tumors in rats and mice and Clara cell toxicity and lung tumors in mice. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity/carcinogenicity and its human relevance. These investigations have revealed significant species differences in coumarin metabolism and toxicity such that the mechanism of coumarin induced effects in rodents, and the relevance of these findings for the safety assessment of coumarin exposure in humans are now better understood. In October 2004, the European Food Safety Authority (EFSA, 2004) reviewed coumarin to establish a tolerable daily intake (TDI) in foods. EFSA issued an opinion indicating that coumarin is not genotoxic, and that a threshold approach to safety assessment was most appropriate. EFSA recommended a TDI of 0 to 0.1 Mg/kg BW/day. Including dietary contributions, the total human exposure is estimated to be 0.06 Mg/kg/day. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. Unlike coumadin and other coumarin derivatives, coumarin has no anti-coagulant activity. However, at low doses (typically 7 to 10 mg/day), coumarin has been used as a 'venotonic' to promote vein health and small venule blood flow. Additionally, coumarin has been used clinically in the treatment of high-protein lymphedema arising from various etiologies. (PMID: 16203076 ).
Structure
Thumb
Synonyms
ValueSource
1,2-BenzopyroneChEBI
2-Propenoic acid, 3-(2-hydroxyphenyl)-, D-lactoneChEBI
2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactoneChEBI
2H-1-Benzopyran-2-oneChEBI
2H-Benzo[b]pyran-2-oneChEBI
5,6-Benzo-2-pyroneChEBI
Benzo-a-pyroneChEBI
Benzo-alpha-pyroneChEBI
cis-O-Coumarinic acid lactoneChEBI
CoumarineChEBI
Coumarinic anhydrideChEBI
CumarinChEBI
O-Hydroxycinnamic acid delta-lactoneChEBI
O-Hydroxycinnamic acid lactoneChEBI
RattexChEBI
Tonka bean camphorChEBI
Venalot monoKegg
2-Propenoate, 3-(2-hydroxyphenyl)-, D-lactoneGenerator
2-Propenoate, 3-(2-hydroxyphenyl)-, delta-lactoneGenerator
2-Propenoate, 3-(2-hydroxyphenyl)-, δ-lactoneGenerator
2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactoneGenerator
Benzo-α-pyroneGenerator
cis-O-Coumarinate lactoneGenerator
O-Hydroxycinnamate delta-lactoneGenerator
O-Hydroxycinnamate δ-lactoneGenerator
O-Hydroxycinnamic acid δ-lactoneGenerator
O-Hydroxycinnamate lactoneGenerator
1, 2-BenzopyroneHMDB
2-oxo-1,2-BenzopyranHMDB
2-oxo-2H-1-BenzopyranHMDB
2H-Chromen-2-oneHMDB
2H-Chromen-2-one (acd/name 4.0)HMDB
KumarinHMDB
O-Hydroxycinnamic lactoneHMDB
O-Hydroxyzimtsaure-lactonHMDB
{2h-benzo[b]pyran-2-one}HMDB
5,6-Benzo-alpha-pyroneHMDB
Chemical FormulaC9H6O2
Average Mass146.1450 Da
Monoisotopic Mass146.03678 Da
IUPAC Name2H-chromen-2-one
Traditional Namecoumarin
CAS Registry Number91-64-5
SMILES
O=C1OC2=CC=CC=C2C=C1
InChI Identifier
InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
InChI KeyZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)V.dorna832021-10-06View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)V.dorna832021-10-06View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)V.dorna832021-10-06View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)V.dorna832021-10-06View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)V.dorna832021-10-06View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)V.dorna832021-10-06View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Varshavi.d262021-10-06View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Varshavi.d262021-10-06View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentus
Actinidia chinensis
Agaricus bisporus
Agave
Allium ampeloprasum
Allium ascalonicum
Allium cepa
Allium cepa L.
Allium fistulosum
Allium sativum
Allium schoenoprasum
Allium tuberosum
Aloysia triphylla
Alyxia lucida-
Amaranthus
Amburana cearensisKNApSAcK Database
Amelanchier alnifolia
Anacardium occidentale
Ananas comosus
Anethum graveolensFooDB
Angelica keiskei
Annona cherimola
Annona muricata
Annona reticulataFooDB
Annona squamosa
Anthriscus cerefolium
Apium graveolensFooDB
Apium graveolens var. dulce
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Arachis hypogaea
Arctium lappa
Armoracia rusticana
Artemisia annuaKNApSAcK Database
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilis
Artocarpus heterophyllus
Asparagus officinalisKNApSAcK Database
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.
Averrhoa carambola
Basella alba
Benincasa hispida
Bertholletia excelsa
Beta vulgaris
Beta vulgaris ssp. cicla
Borago officinalis
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleracea
Brassica oleracea var. botrytis
Brassica oleracea var. capitata
Brassica oleracea var. gemmifera
Brassica oleracea var. gongylodes
Brassica oleracea var. italica
Brassica oleracea var. sabauda
Brassica oleracea var. viridis
Brassica rapa
Brassica rapa ssp. chinensis
Brassica rapa var. pekinensis
Brassica rapa var. rapa
Brassica ruvo
Brosimum alicastrum
Byrsonima crassifolia
Cajanus cajan
Canarium ovatum
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Capparis spinosaFooDB
Capsicum annuum
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carvi
Carya
Carya illinoinensis
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Ceratonia siliqua
Chamaemelum nobile
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chromolaena odorataPlant
Chrysanthemum coronarium
Cicer arietinum
Cichorium endivia
Cichorium intybusFooDB
Cinnamomum
Cinnamomum aromaticumFooDB
Cinnamomum burmannii Nees ex BIKNApSAcK Database
Cinnamomum cassiaKNApSAcK Database
Cinnamomum loureiriiKNApSAcK Database
Cinnamomum verumFooDB
Cirsium
Citrullus lanatus
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifolia
Citrus latifolia
Citrus limonFooDB
Citrus maxima
Citrus paradisi
Citrus reticulata
Citrus X sinensis (L.) Osbeck (pro. sp.)
Cocos nucifera
Coffea arabica L.
Coffea canephora
Colocasia esculenta
Corchorus olitorius
Coriandrum sativum L.
Corylus
Corylus avellana
Crateva religiosa
Crocus sativus
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cuminum cyminum
Curcuma longa
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
Cynara scolymus
Dalea tuberculataKNApSAcK Database
Daucus carotaKNApSAcK Database
Daucus carota ssp. sativusFooDB
Dimocarpus longan
Dioscorea
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Dipteryx odorataKNApSAcK Database
Dipteryx punctataKNApSAcK Database
Durio zibethinus
Dysphania ambrosioides
Elaeis
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
Eragrostis tef
Eriobotrya japonica
Eruca vesicaria subsp. Sativa
Eugenia javanica
Eugenia uniflora
Eupatorium odoratumKNApSAcK Database
Eutrema japonicum
Fagopyrum esculentum
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus caricaFooDB
Ficus simplicissimaKNApSAcK Database
Flammulina velutipes
Foeniculum vulgare
Fragaria x ananassa
Garcinia mangostana
Gaylussacia baccata
Ginkgo bilobaKNApSAcK Database
Glycine max
Gossypium
Grifola frondosa
Hedysarum alpinum
Helianthus annuus L.
Helianthus tuberosus
Hibiscus sabbariffa
Hippophae rhamnoides
Hordeum vulgareFooDB
Hydrocotyle sibthorpioidesKNApSAcK Database
Hypericum japonicumKNApSAcK Database
Hyssopus officinalis L.
Illicium verum
Impatiens siculiferKNApSAcK Database
Ipomoea aquatica
Ipomoea batatas
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.
Juglans regia
Lablab purpureus
Lactuca sativa
Lagenaria siceraria
Lathyrus sativus
Laurus nobilis L.
Lens culinaris
Lentinus edodes
Lepidium sativum
Levisticum officinaleFooDB
Liatris squarrosaKNApSAcK Database
Linum usitatissimum
Litchi chinensis
Luffa aegyptiaca
Lupinus
Lupinus albus
Macadamia
Macadamia tetraphylla
Malpighia emarginata
Malus
Malus pumila
Mammea americana
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativa
Melissa officinalis L.
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicata
Mentha x piperitaFooDB
Mespilus germanica
Metroxylon sagu
Momordica charantia
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Musa acuminata
Musa x paradisiaca
Myrica
Myristica fragrans
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
Nuphar lutea
Ocimum basilicum
Oenothera biennis
Olea europaea
Opuntia
Opuntia cochenillifera
Opuntia macrorhiza
Origanum majorana
Origanum onites
Origanum vulgare
Origanum X majoricum
Oryza rufipogon
Oryza sativa
Pachyrhizus erosus
Panax ginseng
Pangium edule
Panicum miliaceum
Passiflora edulis
Pastinaca sativa
Pediomelum esculentum
Perideridia oregana
Persea americana
Petasites japonicus
Petroselinum crispum
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgaris
Phoenix dactyliferaFooDB
Photinia melanocarpa
Phyllostachys edulis
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Picea abiesKNApSAcK Database
Pimenta dioica
Pimpinella anisumFooDB
Pinus
Pinus edulis
Piper nigrum L.
Pistacia vera
Pisum sativum
Pleurotus ostreatus
Polygonum alpinum
Portulaca oleraceaFooDB
Pouteria sapota
Prunus armeniaca
Prunus avium
Prunus avium L.
Prunus cerasusFooDB
Prunus domestica
Prunus dulcis
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Punica granatum
Pyrus communis
Pyrus pyrifolia
Quercus
Raphanus sativus
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Rheum rhabarbarum
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrum
Ribes uva-crispa
Rosa
Rubus arcticus
Rubus chamaemorus
Rubus idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Salix pulchra
Salvia elegans
Salvia hispanica
Salvia officinalis
Salvia rosmarinus
Sambucus nigra
Sambucus nigra L.
Satureja hortensis L.
Satureja montana
Scabiosa comosaKNApSAcK Database
Scorzonera hispanica
Secale cereale
Sechium edule
Sesamum indicum
Sesbania bispinosa
Sinapis alba
Sisymbrium
Solanum lycopersicum
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicum
Solanum melongena
Solanum quitoense
Solanum tuberosum
Sorbus aucuparia
Sorghum bicolor
Spinacia oleracea
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Taraxacum officinale
Tetragonia tetragonioides
Tetrapanax papyriferPlant
Tetrapanax papyriferusKNApSAcK Database
Thelesperma
Theobroma cacaoFooDB
Thymus capitatusPlant
Thymus pulegioides
Thymus vulgarisFooDB
Tilia cordata
Tilia L.
Tragopogon porrifolius
Tribulus terrestrisPlant
Trigonella foenum-graecumFooDB
Triticum
Triticum aestivum
Triticum durum
Triticum spelta
Triticum turanicum
Typha angustifolia
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarpon
Vaccinium myrtilloides
Vaccinium myrtillus
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaea
Valerianella locusta
Vanilla
Verbascum thapsusKNApSAcK Database
Verbena officinalis
Viburnum edule
Vicia faba
Vigna aconitifolia
Vigna angularis
Vigna mungo
Vigna radiata
Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
Vitis
Vitis aestivalis
Vitis labrusca
Vitis rotundifolia
Vitis vinifera L.FooDB
Xanthosoma sagittifolium
Zea mays L.
Zingiber officinale
Zizania
Zizania aquatica
Ziziphus zizyphus
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
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point71 °Chttps://pubchem.ncbi.nlm.nih.gov/compound/323#section=Melting-Point
Boiling Point301.7 °Chttps://pubchem.ncbi.nlm.nih.gov/compound/323#section=Boiling-Point
Water Solubility1.9 mg/mLNot Available
LogP2.23Not Available
Predicted Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
logP1.72ALOGPS
logP1.78ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.55 m³·mol⁻¹ChemAxon
Polarizability14.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001218
DrugBank IDDB04665
Phenol Explorer Compound ID635
FoodDB IDFDB030742
KNApSAcK IDC00002460
Chemspider ID13848793
KEGG Compound IDC05851
BioCyc IDCOUMARIN
BiGG ID46647
Wikipedia LinkCoumarin
METLIN ID3525
PubChem Compound323
PDB IDNot Available
ChEBI ID28794
Good Scents IDrw1003832
References
General References
  1. Felter SP, Vassallo JD, Carlton BD, Daston GP: A safety assessment of coumarin taking into account species-specificity of toxicokinetics. Food Chem Toxicol. 2006 Apr;44(4):462-75. Epub 2005 Oct 3. [PubMed:16203076 ]
  2. Vocanson M, Valeyrie M, Rozieres A, Hennino A, Floc'h F, Gard A, Nicolas JF: Lack of evidence for allergenic properties of coumarin in a fragrance allergy mouse model. Contact Dermatitis. 2007 Dec;57(6):361-4. doi: 10.1111/j.1600-0536.2007.01276.x. [PubMed:17988284 ]
  3. Coltro WK, Lunte SM, Carrilho E: Comparison of the analytical performance of electrophoresis microchannels fabricated in PDMS, glass, and polyester-toner. Electrophoresis. 2008 Dec;29(24):4928-37. doi: 10.1002/elps.200700897. [PubMed:19025869 ]
  4. Marcolan M, Martins PA, Pedrosa VA, Rodrigues MR, de Oliveira HP, Codognoto L: Spectrofluorimetric determination of coumarin in commercial tablets. J Fluoresc. 2011 Mar;21(2):733-8. doi: 10.1007/s10895-010-0763-5. Epub 2010 Nov 3. [PubMed:21046436 ]
  5. Abraham K, Pfister M, Wohrlin F, Lampen A: Relative bioavailability of coumarin from cinnamon and cinnamon-containing foods compared to isolated coumarin: a four-way crossover study in human volunteers. Mol Nutr Food Res. 2011 Apr;55(4):644-53. doi: 10.1002/mnfr.201000394. Epub 2010 Dec 20. [PubMed:21462332 ]