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(+)-lariciresinol
4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol

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Name:4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
CAS Number: 27003-73-2Picture of molecule3D/inchi
FDA UNII: 73XCE5OZB0
Nikkaji Web:J17.258H
Beilstein Number:4560057
MDL:MFCD07784476
XlogP3-AA:2.40 (est)
Molecular Weight:360.40648000
Formula:C20 H24 O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 568.40 °C. @ 760.00 mm Hg (est)
Flash Point: 568.00 °F. TCC ( 297.60 °C. ) (est)
logP (o/w): 1.640 (est)
Soluble in:
 water, 174.5 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
lariciresinol 98%
BOC Sciences
For experimental / research use only.
Lariciresinol
Coompo
For experimental / research use only.
Lariciresinol from Plants ≥96%
Sigma-Aldrich: Sigma
For experimental / research use only.
(+)-Lariciresinol ≥95.0% (HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (+)-lariciresinol usage levels up to:
 not for fragrance use.
 
Recommendation for (+)-lariciresinol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :332427
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
Chemidplus:0027003732
 
References:
 4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):332427
Pubchem (sid):160645503
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10646
HMDB (The Human Metabolome Database):Search
FooDB:FDB012578
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 capsicum annuum
Search Trop Picture
 elder black elder
Search Trop Picture
 
Synonyms:
4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
 

Articles:

PubMed:[Chemical constituents from ethyl acetate extract of flower of Albizia julibrissin].
PubMed:Inhibition of insect glutathione s-transferase (gst) by conifer extracts.
PubMed:A new lignan glycoside from Forsythia suspensa.
PubMed:Pinoresinol reductase 1 impacts lignin distribution during secondary cell wall biosynthesis in Arabidopsis.
PubMed:Successful expression of a novel bacterial gene for pinoresinol reductase and its effect on lignan biosynthesis in transgenic Arabidopsis thaliana.
PubMed:RNAi-mediated pinoresinol lariciresinol reductase gene silencing in flax (Linum usitatissimum L.) seed coat: consequences on lignans and neolignans accumulation.
PubMed:Steroidal esters from Ferula sinkiangensis.
PubMed:A new lignan glycoside from Trigonostemon heterophyllus.
PubMed:Identification and functional characterization of a flax UDP-glycosyltransferase glucosylating secoisolariciresinol (SECO) into secoisolariciresinol monoglucoside (SMG) and diglucoside (SDG).
PubMed:Bioconversion of pinoresinol into matairesinol by use of recombinant Escherichia coli.
PubMed:Nutritional characterisation and bioactive components of commercial carobs flours.
PubMed:[Chemical constituents from stems of Aquilaria sinensis].
PubMed:Dietary phyto-oestrogens and the risk of ovarian and endometrial cancers: findings from two Australian case-control studies.
PubMed:Lignans 7-hydroxymatairesinol and 7-hydroxymatairesinol 2 exhibit anti-inflammatory activity in human aortic endothelial cells.
PubMed:Structure-plant growth inhibitory activity relationship of lariciresinol.
PubMed:Chemical constituents and biological activities from roots of Enkleia siamensis.
PubMed:Seasonal alteration in amounts of lignans and their glucosides and gene expression of the relevant biosynthetic enzymes in the Forsythia suspense leaf.
PubMed:Role of protein farnesylation events in the ABA-mediated regulation of the Pinoresinol-Lariciresinol Reductase 1 (LuPLR1) gene expression and lignan biosynthesis in flax (Linum usitatissimum L.).
PubMed:Dietary intake and main sources of plant lignans in five European countries.
PubMed:Phenols, lignans and antioxidant properties of legume and sweet chestnut flours.
PubMed:[Chemical constituents from Pachysandra terminalis].
PubMed:Expressed sequence tags and molecular cloning and characterization of gene encoding pinoresinol/lariciresinol reductase from Podophyllum hexandrum.
PubMed:Chemical constituents of the root of Jasminum giraldii.
PubMed:[Chemical constituents from Coptis chinensis].
PubMed:Effect of thermal heating on some lignans in flax seeds, sesame seeds and rye.
PubMed:Antiviral activity of Isatis indigotica root-derived clemastanin B against human and avian influenza A and B viruses in vitro.
PubMed:Dietary intake and major sources of plant lignans in Latvian men and women.
PubMed:Identification and characterization of cis-acting elements involved in the regulation of ABA- and/or GA-mediated LuPLR1 gene expression and lignan biosynthesis in flax (Linum usitatissimum L.) cell cultures.
PubMed:[Chemical constituents from the tubers of Ipomoea batata].
PubMed:Discovery of pinoresinol reductase genes in sphingomonads.
PubMed:Dietary intake of lignans and risk of esophageal and gastric adenocarcinoma: a cohort study in Sweden.
PubMed:Validation of FFQ-based assessment of dietary lignans compared with serum enterolactone in Swedish women.
PubMed:Among plant lignans, pinoresinol has the strongest antiinflammatory properties in human intestinal Caco-2 cells.
PubMed:[Non-alkaloid chemical constituents from Coptis chinensis].
PubMed:Two new diterpenoids from the buds of Wikstroemia chamaedaphne.
PubMed:The effect of light on gene expression and podophyllotoxin biosynthesis in Linum album cell culture.
PubMed:Phenolic compounds from the aerial parts of Diplomorpha canescens.
PubMed:[Studies on chemical constitutes from callus cultures of Stellera chamaejasme].
PubMed:Natural hypolignification is associated with extensive oligolignol accumulation in flax stems.
PubMed:Time-course changes in fungal elicitor-induced lignan synthesis and expression of the relevant genes in cell cultures of Linum album.
PubMed:Estimated intake of dietary phyto-oestrogens in Australian women and evaluation of correlates of phyto-oestrogen intake.
PubMed:Dietary intakes of total and specific lignans are associated with clinical breast tumor characteristics.
PubMed:Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities.
PubMed:Phytoestrogen consumption from foods and supplements and epithelial ovarian cancer risk: a population-based case control study.
PubMed:Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts.
PubMed:Abscisic acid regulates pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol accumulation in developing flax (Linum usitatissimum L.) seeds.
PubMed:Antifungal activity of lariciresinol derived from Sambucus williamsii and their membrane-active mechanisms in Candida albicans.
PubMed:Identification and quantitative determination of lignans in Cedrus atlantica resins using 13C NMR spectroscopy.
PubMed:Identification and quantification of lignans in wheat bran by gas chromatography-electron capture detection.
PubMed:Lignans and neolignans from Stelleropsis antoninae.
PubMed:Effect of dietary intervention on serum lignan levels in pregnant women - a controlled trial.
PubMed:[Chemical constituents of stems and branches of Adina polycephala].
PubMed:Aquilarin A, a new benzenoid derivative from the fresh stem of Aquilaria sinensis.
PubMed:Salicylic acid improves podophyllotoxin production in cell cultures of Linum album by increasing the expression of genes related with its biosynthesis.
PubMed:Pinoresinol-lariciresinol reductases with opposite enantiospecificity determine the enantiomeric composition of lignans in the different organs of Linum usitatissimum L.
PubMed:Assessment of enzyme inhibitory and antioxidant activities of lignans from Taxus baccata L.
PubMed:Crystal structure and catalytic mechanism of leucoanthocyanidin reductase from Vitis vinifera.
PubMed:Structural investigation of biologically active phenolic compounds isolated from European tree species.
PubMed:Metabolic engineering of lignan biosynthesis in Forsythia cell culture.
PubMed:Dietary intake and urinary excretion of lignans in Finnish men.
PubMed:Molecular cloning and characterization of a novel isoflavone reductase-like gene (FcIRL) from high flavonoids-producing callus of Fagopyrum cymosum.
PubMed:The phenylpropanoids of Aster flaccidus.
PubMed:Characterization of variation in the lignan content and composition of winter rye, spring wheat, and spring oat.
PubMed:Quantitative aspects of the metabolism of lignans in pigs fed fibre-enriched rye and wheat bread.
PubMed:Intake of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, and lariciresinol in relation to vascular inflammation and endothelial dysfunction in middle age-elderly men and post-menopausal women living in Northern Italy.
PubMed:[Studies on chemical constituents of aerial parts of Ammopiptanthus mongolicus].
PubMed:Isolation and bioactivities of furfuran type lignan compounds from edible plants.
PubMed:Study of antimalarial activity of chemical constituents from Diospyros quaesita.
PubMed:[Studies on lignan constituents of Clematis parviloba].
PubMed:Lignans and other constituents of the fruits of Euterpe oleracea (Acai) with antioxidant and cytoprotective activities.
PubMed:Dietary consumption of phytochemicals and breast cancer risk in Mexican women.
PubMed:Glycosides from whole plants of Glechoma hederacea L.
PubMed:Dietary lariciresinol attenuates mammary tumor growth and reduces blood vessel density in human MCF-7 breast cancer xenografts and carcinogen-induced mammary tumors in rats.
PubMed:Hinokinin biosynthesis in Linum corymbulosum Reichenb.
PubMed:Stereochemistry of lignans in Phaleria macrocarpa (Scheff.) Boerl.
PubMed:Characterization of Arabidopsis thaliana pinoresinol reductase, a new type of enzyme involved in lignan biosynthesis.
PubMed:Two new phenolic constituents of Humulus japonicus and their cytotoxicity test in vitro.
PubMed:Enhancing lignan biosynthesis by over-expressing pinoresinol lariciresinol reductase in transgenic wheat.
PubMed:Dietary phytoestrogens, including isoflavones, lignans, and coumestrol, in nonvitamin, nonmineral supplements commonly consumed by women in Canada.
PubMed:[Bioactive constituents inhibiting TNF-alpha production in fresh rhizome of Pinellia ternata].
PubMed:Coniferin dimerisation in lignan biosynthesis in flax cells.
PubMed:[Studies on chemical constituents of Sambucus adnata].
PubMed:Lignans from the stems of Sambucus williamsii and their effects on osteoblastic UMR106 cells.
PubMed:A pinoresinol-lariciresinol reductase homologue from the creosote bush (Larrea tridentata) catalyzes the efficient in vitro conversion of p-coumaryl/coniferyl alcohol esters into the allylphenols chavicol/eugenol, but not the propenylphenols p-anol/isoeugenol.
PubMed:[Studies on chemical constituents in root of Isatis indigotica].
PubMed:Assessing phytochemical intake in a group of Mexican women.
PubMed:Relation between plasma enterodiol and enterolactone and dietary intake of lignans in a Dutch endoscopy-based population.
PubMed:Dietary lignan intake and postmenopausal breast cancer risk by estrogen and progesterone receptor status.
PubMed:[Studies on chemical constituents from leaves of Isatis indigotica].
PubMed:[Chemical constituents from water extract of Radix isatidis].
PubMed:(+)-Pinoresinol/(-)-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B.
PubMed:Two new stereoisomers of Tetrahydrofuranoid lignans from the flower buds of Magnolia fargesii.
PubMed:Phenols and lignans from Chenopodium album.
PubMed:Assessing exposure to lignans and their metabolites in humans.
PubMed:Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan.
PubMed:Intakes of 4 dietary lignans and cause-specific and all-cause mortality in the Zutphen Elderly Study.
PubMed:Pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol diglucoside accumulation in developing flax (Linum usitatissimum) seeds.
PubMed:Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester.
PubMed:Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans.
PubMed:Determination of secoisolariciresinol, lariciresinol and isolariciresinol in plant foods by high performance liquid chromatography coupled with coulometric electrode array detection.
PubMed:Antifungal and antibacterial activities of Araucaria araucana (Mol.) K. Koch heartwood lignans.
PubMed:Determination of plant and enterolignans in human serum by high-performance liquid chromatography with tandem mass spectrometric detection.
PubMed:Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry.
PubMed:Isolation of lignans and biological activity studies of Ephedra viridis.
PubMed:Lignans from bark of Larix olgensis var. koreana.
PubMed:Pinoresinol-lariciresinol reductases with different stereospecificity from Linum album and Linum usitatissimum.
PubMed:Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol.
PubMed:Intake of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in Dutch men and women.
PubMed:[Studies on chemical constituents in bark of Larix olgensis var. koreana].
PubMed:New lignan metabolites in rat urine.
PubMed:Crystal structures of apo-form and binary/ternary complexes of Podophyllum secoisolariciresinol dehydrogenase, an enzyme involved in formation of health-protecting and plant defense lignans.
PubMed:Urinary excretion of lignans after administration of isolated plant lignans to rats: the effect of single dose and ten-day exposures.
PubMed:Lignans in resin of Araucaria angustifolia by gas chromatography/mass spectrometry.
PubMed:Bioactive lignans from a cultivar of Helianthus annuus.
PubMed:[The lignins from Torreya grandis cv. Merrilli].
PubMed:Optimization of a liquid chromatography-tandem mass spectrometry method for quantification of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in foods.
PubMed:Anti-ulcerogenic lignans from Taxus baccata L.
PubMed:A new lariciresinol-type butyrolactone lignan derived from hydroxymatairesinol and its identification in spruce wood.
PubMed:Plant lignans in soy-based health supplements.
PubMed:Lipid peroxidation inhibitory compounds from daylily (Hemerocallis fulva) leaves.
PubMed:Liquid chromatography method for plant and mammalian lignans in human urine.
PubMed:Anti-inflammatory and antinociceptive activity of taxoids and lignans from the heartwood of Taxus baccata L.
PubMed:Anti-oxidative activity of glycosides from Ligustrum sinense.
PubMed:[Studies on the lignans from Patrinia scabra].
PubMed:Crystal structures of pinoresinol-lariciresinol and phenylcoumaran benzylic ether reductases and their relationship to isoflavone reductases.
PubMed:Studies on the constituents of Syringa species. XII. New glycosides from the leaves of Syringa reticulata (BLUME) HARA.
PubMed:Potential cancer chemopreventive constituents of the seeds of Dipteryx odorata (tonka bean).
PubMed:Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol.
PubMed:Rye bread in the diet of pigs enhances the formation of enterolactone and increases its levels in plasma, urine and feces.
PubMed:Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds.
PubMed:[Studies on immunocompetent constituents of Patrinia scabra Bunge].
PubMed:Stereochemical diversity in lignan biosynthesis of Arctium lappa L.
PubMed:Short and stereoselective total synthesis of furano lignans (+/-)-dihydrosesamin, (+/-)-lariciresinol dimethyl ether, (+/-)-acuminatin methyl ether, (+/-)-sanshodiol methyl ether, (+/-)-lariciresinol, (+/-)-acuminatin, and (+/-)-lariciresinol monomethyl ether and furofuran lignans (+/-)-sesamin, (+/-)-eudesmin, (+/-)-piperitol methyl ether, (+/-)-pinoresinol, (+/-)-piperitol, and (+/-)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source.
PubMed:Phlomisflavosides A and B, new flavonol bisglycosides from Phlomis spinidens.
PubMed:Lignans from the rhizomes of Coptis japonica differentially act as anti-inflammatory principles.
PubMed:In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol.
PubMed:In situ hybridization and immunolocalization of lignan reductases in woody tissues: implications for heartwood formation and other forms of vascular tissue preservation.
PubMed:Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity.
PubMed:New iridoids from Pedicularis artselaeri.
PubMed:Synthesis of (+)-lariciresinol 3a-acetate, a lignan from Aglaia elaeagnoidea.
PubMed:Justicia lignans VI--prostalidin D, a new arylnaphthalide lignan from Justicia diffusa var. prostrata C.B. Clarke.
PubMed:Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana.
PubMed:Phenylpropanoid derivatives and biflavones at different stages of differentiation and development of Araucaria angustifolia.
PubMed:Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum.
PubMed:Lignans causing photodiscoloration of Tsuga heterophylla: 8-hydroxy-oxomatairesinol from sapwood.
PubMed:Evolution of plant defense mechanisms. Relationships of phenylcoumaran benzylic ether reductases to pinoresinol-lariciresinol and isoflavone reductases.
PubMed:Inhibitory effect of lignans from the rhizomes of Coptis japonica var. dissecta on tumor necrosis factor-alpha production in lipopolysaccharide-stimulated RAW264.7 cells.
PubMed:Recombinant pinoresinol-lariciresinol reductases from western red cedar (Thuja plicata) catalyze opposite enantiospecific conversions.
PubMed:Bisamides, lignans, triterpenes, and insecticidal Cyclopenta[b]benzofurans from Aglaia species.
PubMed:(+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. Protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase.
PubMed:Pharmacologically active components of Todopon Puok (Fagraea racemosa), a medicinal plant from Borneo.
PubMed:Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc.
PubMed:Discovery of natural product chemopreventive agents utilizing HL-60 cell differentiation as a model.
PubMed:Stereospecificity of (+)-pinoresinol and (+)-lariciresinol reductases from Forsythia intermedia.
PubMed:Detection and identification of the plant lignans lariciresinol, isolariciresinol and secoisolariciresinol in human urine.
PubMed:Lariciresinol derivatives from Turrea nilotica and Monechma ciliatum.
PubMed:Plant anticancer agents XXVII: Antileukemic and cytotoxic constituents of Dirca occidentalis (Thymelaeaceae).
 
Notes:
None found
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