(+)-lariciresinol
4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
Identification
| Name | (+)-lariciresinol |
| IUPAC | 4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol |
| CAS Number | 27003-73-2 |
| FDA UNII | 73XCE5OZB0 |
| Molecular Formula | C20 H24 O6 |
| Molecular Weight | 360.40648000 |
| MDL Number | MFCD07784476 |
| Nikkaji Number | J17.258H |
| Beilstein | 4560057 |
Regulatory
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) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
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Potential Uses
Natural Occurrence
Synonyms
4-[[(3R,4R,5S)-5-(4-
hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol
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).