Lamellarin H

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

MedKoo CAT#: 598246

CAS#: 115982-22-4

Description: Lamellarin H is a benzo-isoquinoline-coumarin.


Chemical Structure

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Lamellarin H
CAS# 115982-22-4

Theoretical Analysis

MedKoo Cat#: 598246
Name: Lamellarin H
CAS#: 115982-22-4
Chemical Formula: C25H17NO8
Exact Mass: 459.0954
Molecular Weight: 459.41
Elemental Analysis: C, 65.36; H, 3.73; N, 3.05; O, 27.86

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: Lamellarin H; Lamellarine H;

IUPAC/Chemical Name: 14-(3,4-dihydroxyphenyl)-2,3,11,12-tetrahydroxy-6a,14a-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one

InChi Key: KIRMMCLRVYLQSV-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H17NO8/c27-14-2-1-11(6-15(14)28)21-22-13-8-18(31)19(32)9-20(13)34-25(33)24(22)26-4-3-10-5-16(29)17(30)7-12(10)23(21)26/h1-9,22,24,27-32H

SMILES Code: O=C1OC2=C(C(C13)C(C4=CC=C(O)C(O)=C4)=C5N3C=CC6=C5C=C(O)C(O)=C6)C=C(O)C(O)=C2

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 459.41 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: Dialer C, Imbri D, Hansen SP, Opatz T. Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization. J Org Chem. 2015 Nov 20;80(22):11605-10. doi: 10.1021/acs.joc.5b02194. Epub 2015 Oct 29. PubMed PMID: 26473557.

2: Manjappa KB, Syu JR, Yang DY. Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H. Org Lett. 2016 Jan 15;18(2):332-5. doi: 10.1021/acs.orglett.5b03524. Epub 2016 Jan 7. PubMed PMID: 26741300.

3: You YC, Wang AL, Li DP, Yang G. Pyrrolo[2,1-alpha]isoquinoline as a skeleton for the synthesis of bioactive lamellarin H. Biomed Mater. 2006 Sep;1(3):L7-9. doi: 10.1088/1748-6041/1/3/L01. Epub 2006 Jun 23. PubMed PMID: 18458386.

4: Ridley CP, Reddy MV, Rocha G, Bushman FD, Faulkner DJ. Total synthesis and evaluation of lamellarin alpha 20-Sulfate analogues. Bioorg Med Chem. 2002 Oct;10(10):3285-90. PubMed PMID: 12150874.

5: Li Q, Jiang J, Fan A, Cui Y, Jia Y. Total synthesis of lamellarins D, H, and R and ningalin B. Org Lett. 2011 Jan 21;13(2):312-5. doi: 10.1021/ol1027877. Epub 2010 Dec 17. PubMed PMID: 21175172.

6: B Manjappa K, Lin JM, Yang DY. Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D. J Org Chem. 2017 Jul 21;82(14):7648-7656. doi: 10.1021/acs.joc.7b01061. Epub 2017 Jun 30. PubMed PMID: 28665125.

7: Ishibashi F, Tanabe S, Oda T, Iwao M. Synthesis and structure-activity relationship study of lamellarin derivatives. J Nat Prod. 2002 Apr;65(4):500-4. PubMed PMID: 11975488.

8: Lade DM, Pawar AB, Mainkar PS, Chandrasekhar S. Total Synthesis of Lamellarin D Trimethyl Ether, Lamellarin D, and Lamellarin H. J Org Chem. 2017 May 5;82(9):4998-5004. doi: 10.1021/acs.joc.7b00636. Epub 2017 Apr 24. PubMed PMID: 28421766.