Lariciresinol

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598402

CAS#: 27003-73-2

Description: Lariciresinol is an enterolignan precursor isolated from the herb Sambucus williamsii, a folk medicinal plant used for its therapeutic properties.


Chemical Structure

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Lariciresinol
CAS# 27003-73-2

Theoretical Analysis

MedKoo Cat#: 598402
Name: Lariciresinol
CAS#: 27003-73-2
Chemical Formula: C20H24O6
Exact Mass: 360.1573
Molecular Weight: 360.4
Elemental Analysis: C, 66.65; H, 6.71; O, 26.63

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Lariciresinol; NSC-329247; NSC 329247; NSC329247;

IUPAC/Chemical Name: 4-((2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methoxyphenol

InChi Key: MHXCIKYXNYCMHY-AUSJPIAWSA-N

InChi Code: 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

SMILES Code: OC[C@@H]1[C@@H](C2=CC=C(O)C(OC)=C2)OC[C@@H]1CC3=CC=C(O)C(OC)=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 360.4 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Xiao Y, Ji Q, Gao S, Tan H, Chen R, Li Q, Chen J, Yang Y, Zhang L, Wang Z, Chen W, Hu Z. Combined transcriptome and metabolite profiling reveals that IiPLR1 plays an important role in lariciresinol accumulation in Isatis indigotica. J Exp Bot. 2015 Oct;66(20):6259-71. doi: 10.1093/jxb/erv333. Epub 2015 Jul 10. PubMed PMID: 26163698.

2: Yamauchi S, Kumamoto M, Ochi Y, Nishiwaki H, Shuto Y. Structure-plant growth inhibitory activity relationship of lariciresinol. J Agric Food Chem. 2013 Dec 18;61(50):12297-306. doi: 10.1021/jf404292w. Epub 2013 Dec 4. PubMed PMID: 24274795.

3: Li J, Zhou B, Li C, Chen Q, Wang Y, Li Z, Chen T, Yang C, Jiang Z, Zhong N, Yang Z, Chen R. Lariciresinol-4-O-β-D-glucopyranoside from the root of Isatis indigotica inhibits influenza A virus-induced pro-inflammatory response. J Ethnopharmacol. 2015 Nov 4;174:379-86. doi: 10.1016/j.jep.2015.08.037. Epub 2015 Aug 28. PubMed PMID: 26320688.

4: Hwang B, Cho J, Hwang IS, Jin HG, Woo ER, Lee DG. Antifungal activity of lariciresinol derived from Sambucus williamsii and their membrane-active mechanisms in Candida albicans. Biochem Biophys Res Commun. 2011 Jul 8;410(3):489-93. doi: 10.1016/j.bbrc.2011.06.004. Epub 2011 Jun 7. PubMed PMID: 21679690.

5: Renouard S, Tribalatc MA, Lamblin F, Mongelard G, Fliniaux O, Corbin C, Marosevic D, Pilard S, Demailly H, Gutierrez L, Hano C, Mesnard F, Lainé E. RNAi-mediated pinoresinol lariciresinol reductase gene silencing in flax (Linum usitatissimum L.) seed coat: consequences on lignans and neolignans accumulation. J Plant Physiol. 2014 Sep 15;171(15):1372-7. doi: 10.1016/j.jplph.2014.06.005. Epub 2014 Jun 23. PubMed PMID: 25046758.

6: Ma ZJ, Wang XX, Su G, Yang JJ, Zhu YJ, Wu YW, Li J, Lu L, Zeng L, Pei HX. Proteomic analysis of apoptosis induction by lariciresinol in human HepG2 cells. Chem Biol Interact. 2016 Aug 25;256:209-19. doi: 10.1016/j.cbi.2016.07.011. Epub 2016 Jul 12. PubMed PMID: 27417256.

7: Fang J, Ramsay A, Renouard S, Hano C, Lamblin F, Chabbert B, Mesnard F, Schneider B. Laser Microdissection and Spatiotemporal Pinoresinol-Lariciresinol Reductase Gene Expression Assign the Cell Layer-Specific Accumulation of Secoisolariciresinol Diglucoside in Flaxseed Coats. Front Plant Sci. 2016 Nov 21;7:1743. eCollection 2016. PubMed PMID: 27917190; PubMed Central PMCID: PMC5116464.

8: Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC. Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br J Nutr. 2005 Mar;93(3):393-402. PubMed PMID: 15877880.

9: Renouard S, Corbin C, Lopez T, Montguillon J, Gutierrez L, Lamblin F, Lainé E, Hano C. Abscisic acid regulates pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol accumulation in developing flax (Linum usitatissimum L.) seeds. Planta. 2012 Jan;235(1):85-98. doi: 10.1007/s00425-011-1492-y. Epub 2011 Aug 12. PubMed PMID: 21837520.

10: Roy SC, Rana KK, Guin C. 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. J Org Chem. 2002 May 17;67(10):3242-8. PubMed PMID: 12003531.

11: Corbin C, Decourtil C, Marosevic D, Bailly M, Lopez T, Renouard S, Doussot J, Dutilleul C, Auguin D, Giglioli-Guivarc'h N, Lainé E, Lamblin F, Hano C. 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.). Plant Physiol Biochem. 2013 Nov;72:96-111. doi: 10.1016/j.plaphy.2013.06.001. Epub 2013 Jun 15. PubMed PMID: 23816064.

12: Nishiwaki H, Kumamoto M, Shuto Y, Yamauchi S. Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities. J Agric Food Chem. 2011 Dec 28;59(24):13089-95. doi: 10.1021/jf203222w. Epub 2011 Nov 22. PubMed PMID: 22066904.

13: Saarinen NM, Wärri A, Dings RP, Airio M, Smeds AI, Mäkelä S. 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. Int J Cancer. 2008 Sep 1;123(5):1196-204. doi: 10.1002/ijc.23614. PubMed PMID: 18528864.

14: Wankhede DP, Biswas DK, Rajkumar S, Sinha AK. Expressed sequence tags and molecular cloning and characterization of gene encoding pinoresinol/lariciresinol reductase from Podophyllum hexandrum. Protoplasma. 2013 Dec;250(6):1239-49. doi: 10.1007/s00709-013-0505-z. Epub 2013 May 8. PubMed PMID: 23653238.

15: Hemmati S, von Heimendahl CB, Klaes M, Alfermann AW, Schmidt TJ, Fuss E. Pinoresinol-lariciresinol reductases with opposite enantiospecificity determine the enantiomeric composition of lignans in the different organs of Linum usitatissimum L. Planta Med. 2010 Jun;76(9):928-34. doi: 10.1055/s-0030-1250036. Epub 2010 May 31. PubMed PMID: 20514607.

16: Hemmati S, Schmidt TJ, Fuss E. (+)-Pinoresinol/(-)-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B. FEBS Lett. 2007 Feb 20;581(4):603-10. Epub 2007 Jan 18. PubMed PMID: 17257599.

17: Gang DR, Kasahara H, Xia ZQ, Vander Mijnsbrugge K, Bauw G, Boerjan W, Van Montagu M, Davin LB, Lewis NG. Evolution of plant defense mechanisms. Relationships of phenylcoumaran benzylic ether reductases to pinoresinol-lariciresinol and isoflavone reductases. J Biol Chem. 1999 Mar 12;274(11):7516-27. PubMed PMID: 10066819.

18: Pellegrini N, Valtueña S, Ardigò D, Brighenti F, Franzini L, Del Rio D, Scazzina F, Piatti PM, Zavaroni I. 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. Nutr Metab Cardiovasc Dis. 2010 Jan;20(1):64-71. doi: 10.1016/j.numecd.2009.02.003. Epub 2009 Apr 10. PubMed PMID: 19361969.

19: Fujita M, Gang DR, Davin LB, Lewis NG. Recombinant pinoresinol-lariciresinol reductases from western red cedar (Thuja plicata) catalyze opposite enantiospecific conversions. J Biol Chem. 1999 Jan 8;274(2):618-27. PubMed PMID: 9872995.

20: Rajasekhar D, Subbaraju GV. Synthesis of (+)-lariciresinol 3a-acetate, a lignan from Aglaia elaeagnoidea. J Asian Nat Prod Res. 2000;2(2):153-6. PubMed PMID: 11252680.