(+)-lariciresinol (CED0007919)

Record Information
Version1.0
Creation Date2016-05-27 01:39:54 UTC
Update Date2026-04-06 16:57:06 UTC
Accession NumberCHEM041706
Identification
Common Name(+)-lariciresinol
ClassSmall Molecule
Description
(+)-lariciresinol is an organic compound with the formula C20H24O6 and an average molecular weight of 360.40 g/mol. (+)-lariciresinol belongs to the tetrahydrofuran lignans, a subclass of furanoid lignans within the organic compounds. This compound is identified in two recorded sources related to food, food processing, and cookware, specifically in the preparation of wort and the preparation of wine or sparkling wine.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LariciresinolChEBI
Larici-resinolMeSH
tetrahydro-2-(4-Hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanmethanolMeSH
(+)-LariciresinolPhytoBank
Chemical FormulaC20H24O6
Average Molecular Mass360.401 g/mol
Monoisotopic Mass360.157 g/mol
CAS Registry Number27003-73-2
IUPAC Name4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol
Traditional Namelariciresinol
SMILESCOC1=C(O)C=CC(C[C@H]2CO[C@@H]([C@H]2CO)C2=CC(OC)=C(O)C=C2)=C1
InChI IdentifierInChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
InChI KeyMHXCIKYXNYCMHY-AUSJPIAWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct Parent7,9'-epoxylignans
Alternative Parents
Substituents
  • 7,9p-epoxylignan
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tetrahydrofuran
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP2.16ALOGPS
logP2.31ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.75ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area88.38 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.19 m³·mol⁻¹ChemAxon
Polarizability38.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-0119000000-1b51be74b31ac9d7b539Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03du-0779000000-e7be7d105b100a9c3b9cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01p9-1910000000-b979ee1e05cf5260eb79Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-7a840402d6d204c9b8c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bvl-0019000000-ef7220328296c1790e21Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ikl-1926000000-30d6a96496d1ab30c241Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0039000000-bb1d565a494ee8df519aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0967000000-392787799b00541a0644Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002r-1924000000-af0c5df11ebeae93db35Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-2acd137877feef0611c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bvl-0009000000-d37a341dfd5a59b2d9baNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0269000000-23623d625c8571548180Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2308.0Log mg/kg[1300:4100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureMonocarboxylate transporter 8P36021HumansPredicted (SEA)0.233548
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)233.626
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)5.60514
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)34.3315
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)8.32987
Click to view 3D structureSolute carrier organic anion transporter family member 2B1O94956HumansPredicted (SEA)9.41976
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)208.247
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)69.1301
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)113.893
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)36.667
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)42.8949
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)208.169
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)71.6213
Click to view 3D structurePROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)P96878Mycobacterium tuberculosisPredicted (SEA)40.0145
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)115.684
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansPredicted (SEA)30.5947
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)449.735
Tissue factor structureClick to view 3D structureTissue factorP13726HumansPredicted (SEA)30.6726
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)217.277
Click to view 3D structureTyrosinaseO42713Agaricus bisporusPredicted (SEA)12.0666
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)1311.29
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)53.7938
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)282.904
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)1118.62
Click to view 3D structureLarge T antigenP03070Simian virus 40Predicted (SEA)24.7561
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0303941
FooDB IDFDB030072
Phenol Explorer IDNot Available
KNApSAcK IDC00000603
BiGG IDNot Available
BioCyc IDCPD-8907
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLariciresinol
Chemspider ID294521
ChEBI ID67246
PubChem Compound IDNot Available
Kegg Compound IDC10646
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21138310
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21679690
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21973054
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22218086
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8262939