AFCDB: (+)-lariciresinol (FDB030072)

Record Information

Version

1.0

Creation date

2015-05-07 18:33:24 UTC

Update date

2020-09-17 15:31:41 UTC

Primary ID

FDB030072

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(+)-lariciresinol

Description

(+)-Lariciresinol 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 positons 2, 3 and 4, respectively. (+)-Lariciresinol has been detected in several different foods, such as parsnips, white mustards, narrowleaf cattails, turnips, and common sages. This could make (+)-Lariciresinol a potential biomarker for the consumption of these foods. Lariciresinol is also found in sesame seeds, Brassica vegetables, in the bark and wood of white fir (Abies alba).

CAS Number

27003-73-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.31	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	97.19 m³·mol⁻¹	ChemAxon
Polarizability	38.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C20H24O6

IUPAC name

4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol

InChI Identifier

InChI=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 Key

MHXCIKYXNYCMHY-AUSJPIAWSA-N

Isomeric SMILES

COC1=C(O)C=CC(C[C@H]2CO[C@@H]([C@H]2CO)C2=CC(OC)=C(O)C=C2)=C1

Average Molecular Weight

360.401

Monoisotopic Molecular Weight

360.1572885

Classification

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.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,9'-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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:67246 )
phenols (CHEBI:67246 )
primary alcohol (CHEBI:67246 )
oxolanes (CHEBI:67246 )
lignan (CHEBI:67246 )
Lignans (C10646 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(+)-lariciresinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(+)-lariciresinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(+)-lariciresinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(+)-lariciresinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(+)-lariciresinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(+)-lariciresinol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(+)-lariciresinol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0119000000-1b51be74b31ac9d7b539	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03du-0779000000-e7be7d105b100a9c3b9c	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p9-1910000000-b979ee1e05cf5260eb79	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-7a840402d6d204c9b8c7	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bvl-0019000000-ef7220328296c1790e21	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ikl-1926000000-30d6a96496d1ab30c241	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0039000000-bb1d565a494ee8df519a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0967000000-392787799b00541a0644	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-1924000000-af0c5df11ebeae93db35	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-2acd137877feef0611c1	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bvl-0009000000-d37a341dfd5a59b2d9ba	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0269000000-23623d625c8571548180	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

(+)-lariciresinol (FDB030072)

Structure for FDB030072 ((+)-lariciresinol)