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Record Information
Version1.0
Created at2007-01-23 13:27:56 UTC
Updated at2024-05-13 01:12:52 UTC
NP-MRD IDNP0000011
Secondary Accession NumbersNone
Natural Product Identification
Common NameEugenol
DescriptionEugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from guaiacol, with an allyl chain positioned para to the hydroxy group. It is soluble in water, alcohol, chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol is widely distributed in plants. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://Doi.Org/10.1021/Ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID:15089054  ; PMID:935250  ) And acts as positive allosteric modulators of the GABA-A receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID:27771920  ).
Structure
Thumb
Synonyms
ValueSource
1,3,4-EugenolChEBI
1-Allyl-3-methoxy-4-hydroxybenzeneChEBI
1-Allyl-4-hydroxy-3-methoxybenzeneChEBI
1-Hydroxy-2-methoxy-4-allylbenzeneChEBI
1-Hydroxy-2-methoxy-4-prop-2-enylbenzeneChEBI
1-Hydroxy-2-methoxy-4-propenylbenzeneChEBI
2-Hydroxy-5-allylanisoleChEBI
2-Methoxy-1-hydroxy-4-allylbenzeneChEBI
2-Methoxy-4-(2-propen-1-yl)phenolChEBI
2-Methoxy-4-(2-propenyl)phenolChEBI
2-Methoxy-4-allylphenolChEBI
2-Methoxy-4-prop-2-enylphenolChEBI
4-Allyl-1-hydroxy-2-methoxybenzeneChEBI
4-Allyl-2-methoxyphenolChEBI
4-Allylcatechol-2-methyl etherChEBI
4-AllylguaiacolChEBI
4-Hydroxy-3-methoxy-1-allylbenzeneChEBI
AllylguaiacolChEBI
Caryophyllic acidChEBI
Eugenic acidChEBI
p-AllylguaiacolChEBI
p-EugenolChEBI
CaryophyllateGenerator
EugenateGenerator
2-Methoxy-4-(3-propenyl)phenolHMDB
2-Methoxy-4-(prop-2-en-1-yl)phenolHMDB
4-Allyl-2-methoxy-phenolHMDB
4-Allylcatechol 2-methyl etherHMDB
4-Hydroxy-3-methoxyallylbenzeneHMDB
5-AllylguaiacolHMDB
EngenolHMDB
Eugenol (natural)HMDB
Synthetic eugenolHMDB
2-Methoxy-4-(2'-propenyl)phenolPhytoBank
2-Methoxy-4-(2’-propenyl)phenolPhytoBank
2-Methoxy-4-[2-allyl]phenolPhytoBank
3-(3-Methoxy-4-hydroxyphenyl)propenePhytoBank
3-(4-Hydroxy-3-methoxyphenyl)-1-propenePhytoBank
4-AllenylguaiacolPhytoBank
Chemical FormulaC10H12O2
Average Mass164.2011 Da
Monoisotopic Mass164.08373 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number97-53-0
SMILESNot Available
InChI Identifier
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChI KeyRRAFCDWBNXTKKO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D_DEPT NMR13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)shaolidong@ynutcm.edu.cnNot AvailableNot Available2024-05-11View Spectrum
1D_DEPT NMR13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)shaolidong@ynutcm.edu.cnNot AvailableNot Available2024-05-11View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)shaolidong@ynutcm.edu.cnNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)shaolidong@ynutcm.edu.cnNot AvailableNot Available2024-05-11View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500.33, CDCl3, simulated)Not AvailableNot AvailableNot Available2024-05-11View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentus
Abutilon indicumPlant
Achillea abrotanoides
Achillea fragrantissimaPlant
Achillea grandifolia
Achillea millefoliumPlant
Achillea moschataPlant
Acorus calamusPlant
Acorus gramineus
Acorus tatarinowiiPlant
Actinidia chinensis
Aegle marmelosPlant
Agaricus bisporus
Agastache foeniculum
Agastache rugosa
Agathosma betulina
Agave
Ageratina conyzoidesPlant
Ageratum conyzoides
Allium ampeloprasum
Allium ascalonicum
Allium cepa
Allium cepa L.
Allium fistulosum
Allium sativum
Allium schoenoprasum
Allium tuberosum
Aloysia triphylla
Alphinia galanga-
Alpinia chinensis
Alpinia conchigera
Alpinia galangaPlant
Alpinia officinarumPlant
Amaranthus
Amauris echeria
Amelanchier alnifolia
Anacardium occidentale
Ananas comosus
Anethum graveolensFooDB
Angelica keiskei
Annona cherimola
Annona muricata
Annona reticulata
Annona squamosa
Anthriscus cerefolium
Anthriscus sylvestris
Apium graveolensFooDB
Apium graveolens var. dulce
Apium graveolens var. rapaceum
Apium graveolens var. secalinum
Arachis hypogaea
Arctium lappa
Armoracia rusticana
Artemisia annuaPlant
Artemisia capillarisPlant
Artemisia dracunculusFooDB
Artemisia japonica
Artemisia klotzchianaPlant
Artemisia scopariaPlant
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllus
Asarum canadense
Asarum fauriei
Asarum forbesiiPlant
Asarum hexalobum
Asarum sieboldiiPlant
Aspalathus linearis
Asparagus officinalis
Aster scaber
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativa L.
Averrhoa carambola
Baeckea frutescens-
Basella alba
Bellis perennis
Benincasa hispida
Bertholletia excelsa
Beta vulgarisPlant
Beta vulgaris ssp. cicla
Bidens tripartita
Blepharocalyx salicifolius
Blumea mollis
Borago officinalis
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleracea
Brassica oleracea var. botrytisFooDB
    • L. Valettea X. Fernandez, S. Poulain, A.-M. Loiseau, L. Lizzani-Cuvelier, R. Levieil, L. Restier....
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
Bupleurum chinensePlant
Byrsonima crassifolia
Caesulia axillaris
Cajanus cajan
Calamintha nepeta subsp. glandulosaPlant
Callicarpa japonica
Camellia sasanqua
Cananga odorata
Canarium ovatum
Canella winterana
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibarius
Cantinoa americana
Capparis spinosa
Capsicum annuumFooDB
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carviFooDB
Carya
Carya illinoinensis
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Castanopsis cuspidata
Cedronella canariensis
Ceratonia siliqua
Cestrum nocturnumPlant
Chaerophyllum bulbosum
Chamaemelum nobile
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chrysanthemum coronarium
Cicer arietinum
Cichorium endivia
Cichorium intybus
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum burmanni
Cinnamomum camphoraPlant
Cinnamomum illicioidesPlant
Cinnamomum japonicumPlant
Cinnamomum parthenoxylumPlant
Cinnamomum sieboldii
Cinnamomum spp.Plant
Cinnamomum subaveniumPlant
Cinnamomum tamalaPlant
Cinnamomum verumFooDB
Cirsium
Cistus creticusPlant
Citrullus lanatus
Citrus ×limon (L.) Burm. f. (pro sp.)
Citrus aurantiifolia
Citrus latifolia
Citrus limon
Citrus maxima
Citrus paradisi
Citrus reticulata
Citrus X sinensis (L.) Osbeck (pro. sp.)
Clinopodium serpyllifolium
Cocos nucifera
Coffea arabica L.FooDB
Coffea canephora
Coleus amboinicus
Coleus aromaticusPlant
Colocasia esculenta
Coluria geoides
Commiphora mukulPlant
Commiphora myrrhaPlant
Corchorus olitorius
Coriandrum sativum L.FooDB
Corylus
Corylus avellana
Crateva religiosa
Crocus sativus
Croton conduplicatus
Cucumis melo
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblonga
Cymbopogon citratus
Cymbopogon flexuosus
Cymbopogon nardus
Cynara cardunculus
Cynara scolymus
Cyphomandra betacea
Dahlia sherffii
Damburneya purpurea
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Delphinium yunnanensePlant
Dianthus chinensisPlant
Dimocarpus longan
Dioscorea
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Durio zibethinus
Dysphania ambrosioides
Echinophora tenuifolia
Elaeis
Eleocharis dulcis
Elettaria cardamomum
Elsholtzia blanda
Empetrum nigrum
Eragrostis tef
Erigeron philadelphicus
Eriobotrya japonica
Eruca vesicaria subsp. Sativa
Eucalyptus brassiana
Eucalyptus polyanthemos
Eugenia javanica
Eugenia uniflora
Eutrema japonicum
Fagopyrum esculentum
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus caricaFooDB
Flammulina velutipes
Foeniculum vulgareFooDB
Fragaria x ananassa
fragrans
      Not Available
Garcinia mangostana
Gaylussacia baccata
Geum heterocarpum
Ginkgo biloba
Glycine maxFooDB
Gossypium
Grifola frondosa
Gundelia tournefortii
Hamamelis virginiana
Hedysarum alpinum
Helianthus annuus
Helianthus annuus L.FooDB
Helianthus tuberosus
Heracleum antasiaticum
Hesperis matronalisPlant
Hibiscus sabbariffaFooDB
Hippophae rhamnoides
Hordeum vulgare
Hyptis suaveolens
Hyssopus officinalis L.FooDB
Ilex paraguariensis
Illicium anisatum
Illicium verumFooDB
Ipomoea aquatica
Ipomoea batatas
Ipomoea pes-caprae
Jackiella javanica-
Jasminum grandiflorumPlant
Jasminum polyanthum
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.
Juglans regiaFooDB
Lablab purpureus
Lactuca sativa
Lagenaria siceraria
Lantana camara
Laser trilobum
Lathyrus sativus
Laurus nobilis
Laurus nobilis L.FooDB
Lavandula angustifolia
Lens culinaris
Lentinus edodes
Leonurus sibiricus
Lepidium sativum
Levisticum officinaleFooDB
Lindera neesiana
Linum usitatissimum
Lippia javanicaPlant
Lippia nodiflora
Lippia origanoides
Litchi chinensis
Litsea cubebaPlant
Lonicera japonicaPlant
Luffa aegyptiaca
Lupinus
Lupinus albus
Macadamia
Macadamia tetraphylla
Magnolia lilifloraPlant
Malpighia emarginata
Malus
Malus pumila
Mammea americana
Mandragora autumnalisPlant
Mandragora officinarum
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria recutita
Matteuccia struthiopteris
Medicago sativa
Melissa officinalis L.FooDB
Mentha
Mentha aquatica
Mentha arvensisFooDB
Mentha rotundifolia
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanica
Metroxylon sagu
Michelia alba
Michelia compressa
Momordica charantia
Morchellaceae
Morella rubra
Morina persica
Moringa oleiferaPlant
Moringa peregrinaPlant
Morus
Morus albaPlant
Morus nigra
Mosla chinensisPlant
Murraya paniculataPlant
Musa acuminataFooDB
Musa paradisiaca
Musa x paradisiaca
Myrica
Myristica fragransFooDB
Myrtus communis
Narcissus tazetta var.chinensisPlant
Nectandra hihua
Nelumbo
Nelumbo nucifera
Nemuaron vieillardii
Nepeta catariaPlant
Nephelium lappaceum
Nicotiana bonariensisPlant
Nuphar lutea
Ocimum americanum
Ocimum basilicumFooDB
Ocimum campechianum
Ocimum gratissimum
Ocimum kilimandscharicum
Ocimum selloi
Ocimum spp.Plant
Ocimum tenuiflorumPlant
Oenothera biennis
Olea europaea
Ononis natrix
Opuntia
Opuntia cochenillifera
Opuntia macrorhiza
Origanum acutidens
Origanum majoranaFooDB
Origanum minutiflorum
Origanum onitesFooDB
Origanum ramonense
Origanum vulgareFooDB
Origanum X majoricum
Oryza rufipogon
Oryza sativa
Pachyrhizus erosus
Paeonia lactiflora
Panax ginseng
Pandanus tectorius
Pangium edule
Panicum miliaceum
Passiflora edulis
Passiflora incarnata
Pastinaca sativa
Pediomelum esculentum
Peperomia blanda
Peperomia suiPlant
Perideridia oregana
Perilla frutescens
Perilla frutescens var.acutaPlant
Persea americana
Petasites japonicus
Petroselinum crispumPlant
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgaris
Phoenix dactylifera
Photinia melanocarpa
Phyllostachys edulis
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Pimenta dioicaFooDB
Pimenta racemosa
Pimpinella anisumFooDB
Pinus
Pinus edulis
Piper auritum
Piper betlePlant
Piper guineense
Piper nigrum
Piper nigrum L.FooDB
Piper sanctum
Piper sylvestre
Piper taiwanensePlant
Pistacia vera
Pisum sativum
Plantago lanceolataPlant
Platostoma africanum
Plectranthus marrubioidesPlant
Pleurotus ostreatus
Pogostemon cablinPlant
Polygala senega
Polygonum alpinum
Portulaca oleracea
Pouteria sapota
Prunus armeniaca
Prunus avium
Prunus avium L.
Prunus cerasusFooDB
Prunus domestica
Prunus dulcisFooDB
Prunus persica
Prunus persica var. nucipersica
Prunus persica var. persica
Prunus tomentosa
Prunus virginiana
Psidium cattleianum
Psidium guajavaFooDB
Psophocarpus tetragonolobus
Pulicaria paludosa
Punica granatum
Pyrus communis
Pyrus pyrifoliaFooDB
    • Gary R. Takeoka, Ron G. Buttery, and Robert A. Flath. Volatile Constituents of Asian Pear (Pyrus ...
Quercus
Quercus agrifolia
Raphanus sativus
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Rhanterium epapposum
Rheum rhabarbarum
Ribes aureum
Ribes glandulosum
Ribes nigrum
Ribes rubrum
Ribes uva-crispa
Riccardia multifida
Riccardia multifida subsp. DecrescensPlant
Rosa
Rosa gallica
Rosa rugosaPlant
Rubus arcticus
Rubus chamaemorus
Rubus idaeus
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Salix aegyptiacaPlant
Salix pulchra
Salvadora persica
Salvia caespitosa
Salvia elegans
Salvia hispanica
Salvia iodantha
Salvia officinalis
Salvia rosmarinusFooDB
Sambucus nigra
Sambucus nigra L.
Sassafras albidum
Sassafras randaiensePlant
Sassafras randainensePlant
Sassafras tzumuPlant
Satureja hortensis L.
Satureja montana
Scorzonera hispanica
Scrophularia amplexicaulisPlant
Scrophularia oxysepalaPlant
Scutellaria baicalensis
Scutellaria barbata
Secale cereale
Sechium edule
Sesamum indicum
Sesbania bispinosa
Sideritis chamaedrifolia
Sideritis tragoriganum
Sinapis albaFooDB
Siphonostegia chinensisPlant
Sisymbrium
Solanum lycopersicum
Solanum lycopersicum var. cerasiforme
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongena
Solanum quitoense
Solanum tuberosum
Sorbus aucuparia
Sorghum bicolor
Spathiphyllum cannifolium
Spinacia oleracea
Stachys atherocalyx
Stachys recta
Stevia rebaudiana
Strobilanthes crispusPlant
Swertia japonica
Syzygium aromaticumFooDB
Syzygium cumini
Syzygium jambos
Tamarindus indica
Tanacetum macrophyllumPlant
Tanacetum parthenium
Tanacetum vulgare
Taraxacum officinale
Tasmannia lanceolata
Taxus canadensis
Taxus cuspidata
Taxus wallichianaPlant
Terminalia chebulaPlant
Tetragonia tetragonioides
Thelesperma
Thymbra capitata
Thymbra spicata
Thymus broussonettiPlant
Thymus capitatusPlant
Thymus maroccanusPlant
Thymus praecosPlant
Thymus pulegioides
Thymus revolutus
Thymus vulgarisFooDB
Tilia cordata
Tilia L.FooDB
Toddalia asiaticaPlant
Tragopogon porrifolius
Trigonella foenum-graecum
Tripleurospermum maritimum
Triticum
Triticum aestivum
Triticum durum
Triticum spelta
Triticum turanicum
Typha angustifolia
Ulva pertusa-
Umbellularia californica
Uvariopsis tripetala
Vaccinium
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium ashei
Vaccinium corymbosumFooDB
Vaccinium deliciosum
Vaccinium elliottii
Vaccinium macrocarponFooDB
Vaccinium myrtilloides
Vaccinium myrtillusFooDB
Vaccinium ovalifolium
Vaccinium ovatum
Vaccinium oxycoccos
Vaccinium parvifolium
Vaccinium reticulatum
Vaccinium stamineum
Vaccinium uliginosum
Vaccinium vitis-idaea
Vachellia rigidula
Valerianella locusta
Vanilla
Verbena officinalis
Veronica spicataPlant
Viburnum edule
Vicia faba
Vigna aconitifolia
Vigna angularis
Vigna mungo
Vigna radiataFooDB
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
Vitis vinifera L.
Xanthosoma sagittifolium
Zea mays L.FooDB
Zieria smithii
Zingiber mioga
Zingiber officinaleFooDB
Zizania
Zizania aquatica
Ziziphus zizyphus
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-7.5 °Chttps://en.wikipedia.org/wiki/Eugenol
Boiling Point254 °Chttps://en.wikipedia.org/wiki/Eugenol
Water Solubility2.46 mg/mLNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
HMDB IDHMDB0005809
DrugBank IDDB09086
Phenol Explorer Compound ID646
FoodDB IDFDB012171
KNApSAcK IDC00000619
Chemspider ID13876103
KEGG Compound IDC10453
BioCyc IDCPD-6481
BiGG IDNot Available
Wikipedia LinkEugenol
METLIN ID4022
PubChem Compound3314
PDB IDEOL
ChEBI ID4917
Good Scents IDNot Available
References
General References
  1. Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS: Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases. Drug Dev Ind Pharm. 2004 Feb;30(2):195-203. doi: 10.1081/ddc-120028715. [PubMed:15089054 ]
  2. Sell AB, Carlini EA: Anesthetic action of methyleugenol and other eugenol derivatives. Pharmacology. 1976;14(4):367-77. doi: 10.1159/000136617. [PubMed:935250 ]
  3. Fujisawa S, Murakami Y: Eugenol and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:45-66. doi: 10.1007/978-3-319-41342-6_3. [PubMed:27771920 ]
  4. Guironnet G, Dalbiez-Gauthier C, Rousset F, Schmitt D, Peguet-Navarro J: In vitro human T cell sensitization to haptens by monocyte-derived dendritic cells. Toxicol In Vitro. 2000 Dec;14(6):517-22. doi: 10.1016/s0887-2333(00)00043-6. [PubMed:11033063 ]
  5. Fujisawa S, Okada N, Muraoka E: Comparative effects of eugenol to bis-eugenol on oral mucous membranes. Dent Mater J. 2001 Sep;20(3):237-42. doi: 10.4012/dmj.20.237. [PubMed:11806158 ]
  1. Xiao WW, Zhang HL, Wang CF, Chen Y, Zhan R, Li D, Shao LD: Chemical Synthesis Enables the Configurational Determination of Myristriol, a Highly Oxygenated Phenylpropanoid from Myristica fragrans Houtt. Chem Biodivers. 2023 Mar;20(3):e202201075. doi: 10.1002/cbdv.202201075. Epub 2023 Feb 20. [PubMed:36762483 ]