Licarin A | CAS#51020-86-1 | neolignan

MedKoo Cat#: 598817 | Name: Licarin A

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Description:

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

Licarin A is a neolignan isolated from various plants.

Chemical Structure

Licarin A

CAS#51020-86-1 (rotation -)

Theoretical Analysis

MedKoo Cat#: 598817

Name: Licarin A

CAS#: 51020-86-1 (rotation -)

Chemical Formula: C20H22O4

Exact Mass: 326.1518

Molecular Weight: 326.39

Elemental Analysis: C, 73.60; H, 6.79; O, 19.61

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Related CAS #

83377-50-8 (rotation +) 51020-86-1 (rotation -)

Synonym

Licarin A; NSC 370989; NSC-370989; NSC370989; (-)-Licarin A;

IUPAC/Chemical Name

2-methoxy-4-((2R,3R)-7-methoxy-3-methyl-5-((E)-prop-1-en-1-yl)-2,3-dihydrobenzofuran-2-yl)phenol

InChi Key

ITDOFWOJEDZPCF-OTBILJLCSA-N

InChi Code

InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+/t12-,19-/m1/s1

SMILES Code

OC1=CC=C([C@@H]2OC3=C(OC)C=C(/C=C/C)C=C3[C@H]2C)C=C1OC

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 326.39 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.

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

1: Matsui T, Ito C, Masubuchi S, Itoigawa M. Licarin A is a candidate compound for the treatment of immediate hypersensitivity via inhibition of rat mast cell line RBL-2H3 cells. J Pharm Pharmacol. 2015 Dec;67(12):1723-32. doi: 10.1111/jphp.12475. Epub 2015 Sep 17. PubMed PMID: 26376734. 2: Néris PL, Caldas JP, Rodrigues YK, Amorim FM, Leite JA, Rodrigues-Mascarenhas S, Barbosa-Filho JM, Rodrigues LC, Oliveira MR. Neolignan Licarin A presents effect against Leishmania (Leishmania) major associated with immunomodulation in vitro. Exp Parasitol. 2013 Oct;135(2):307-13. doi: 10.1016/j.exppara.2013.07.007. Epub 2013 Jul 24. PubMed PMID: 23891943. 3: León-Díaz R, Meckes-Fischer M, Valdovinos-Martínez L, Campos MG, Hernández-Pando R, Jiménez-Arellanes MA. Antitubercular activity and the subacute toxicity of (-)-Licarin A in BALB/c mice: a neolignan isolated from Aristolochia taliscana. Arch Med Res. 2013 Feb;44(2):99-104. doi: 10.1016/j.arcmed.2012.12.006. Epub 2013 Jan 4. PubMed PMID: 23291382. 4: Pereira AC, Magalhães LG, Januário AH, Pauletti PM, Cunha WR, Bastos JK, Nanayakkara DN, Silva ML. Enantiomeric resolution of (±)-licarin A by high-performance liquid-chromatography using a chiral stationary phase. J Chromatogr A. 2011 Sep 28;1218(39):7051-4. doi: 10.1016/j.chroma.2011.07.093. Epub 2011 Aug 6. PubMed PMID: 21868019. 5: Li F, Yang XW. Simultaneous determination of diastereomers (+)-licarin A and isolicarin A from Myristica fragrans in rat plasma by HPLC and its application to their pharmacokinetics. Planta Med. 2008 Jun;74(8):880-4. doi: 10.1055/s-2008-1074545. Epub 2008 Jun 3. PubMed PMID: 18523922. 6: Pereira AC, Magalhães LG, Gonçalves UO, Luz PP, Moraes AC, Rodrigues V, da Matta Guedes PM, da Silva Filho AA, Cunha WR, Bastos JK, Nanayakkara NP, e Silva ML. Schistosomicidal and trypanocidal structure-activity relationships for (±)-licarin A and its (-)- and (+)-enantiomers. Phytochemistry. 2011 Aug;72(11-12):1424-30. doi: 10.1016/j.phytochem.2011.04.007. Epub 2011 May 11. PubMed PMID: 21570099. 7: Ma CJ, Kim SR, Kim J, Kim YC. Meso-dihydroguaiaretic acid and licarin A of Machilus thunbergii protect against glutamate-induced toxicity in primary cultures of a rat cortical cells. Br J Pharmacol. 2005 Nov;146(5):752-9. PubMed PMID: 16151440; PubMed Central PMCID: PMC1751201. 8: Cabral MM, Barbosa-Filho JM, Maia GL, Chaves MC, Braga MV, De Souza W, Soares RO. Neolignans from plants in northeastern Brazil (Lauraceae) with activity against Trypanosoma cruzi. Exp Parasitol. 2010 Mar;124(3):319-24. doi: 10.1016/j.exppara.2009.11.007. Epub 2009 Nov 26. PubMed PMID: 19944690. 9: Chiu S, Wang T, Belski M, Abourashed EA. HPLC-Guided Isolation, Purification and Characterization of Phenylpropanoid and Phenolic Constituents of Nutmeg Kernel (Myristica fragrans). Nat Prod Commun. 2016 Apr;11(4):483-8. PubMed PMID: 27396199; PubMed Central PMCID: PMC4943679. 10: Barros LF, Barison A, Salvador MJ, de Mello-Silva R, Cabral EC, Eberlin MN, Stefanello ME. Constituents of the leaves of Magnolia ovata. J Nat Prod. 2009 Aug;72(8):1529-32. doi: 10.1021/np900203y. PubMed PMID: 19658431. 11: Cabral MM, Azambuja P, Gottlieb OR, Garcia ES. Effects of some lignans and neolignans on the development and excretion of Rhodnius prolixus. Fitoterapia. 2000 Feb;71(1):1-9. PubMed PMID: 11449462. 12: Maheswari U, Ghosh K, Sadras SR. Licarin A induces cell death by activation of autophagy and apoptosis in non-small cell lung cancer cells. Apoptosis. 2018 Apr;23(3-4):210-225. doi: 10.1007/s10495-018-1449-8. Erratum in: Apoptosis. 2018 Mar 15;:. PubMed PMID: 29468481. 13: Garcia ES, Azambuja P. Lignoids in insects: chemical probes for the study of ecdysis, excretion and Trypanosoma cruzi-triatomine interactions. Toxicon. 2004 Sep 15;44(4):431-40. Review. PubMed PMID: 15302525. 14: Yoon D, Imran KM, Kim YS. Distinctive effects of licarin A on lipolysis mediated by PKA and on formation of brown adipocytes from C3H10T1/2 mesenchymal stem cells. Toxicol Appl Pharmacol. 2018 Feb 1;340:9-20. doi: 10.1016/j.taap.2017.12.015. Epub 2017 Dec 27. PubMed PMID: 29288687.