Danicalipin A | CAS#unknown | Lipid bilayer modulator

MedKoo Cat#: 463320 | Name: Danicalipin A

Description:

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

Danicalipin A is a lipid bilayer modulator which likely inserts into lipid bilayers in the headgroup region, alters their structure and phase behavior, thins the bilayer and fluidizes it, allowing even saturated lipid to form fluid bilayers.

Chemical Structure

Danicalipin A

CAS#unknown

Theoretical Analysis

MedKoo Cat#: 463320

Name: Danicalipin A

CAS#: unknown

Chemical Formula: C22H38Cl6Na2O8S2

Exact Mass: 749.9935

Molecular Weight: 753.34

Elemental Analysis: C, 35.08; H, 5.08; Cl, 28.23; Na, 6.10; O, 16.99; S, 8.51

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Danicalipin A; Danicalipin-A;

IUPAC/Chemical Name

sodium (11S,13R,14R,15S,16R)-2,2,11,13,15,16-hexachlorodocosane-1,14-diyl bis(sulfate)

InChi Key

HTDOYZCTMWIBFD-WDLPQXGQSA-L

InChi Code

InChI=1S/C22H40Cl6O8S2.2Na/c1-2-3-4-10-13-18(24)20(26)21(36-38(32,33)34)19(25)15-17(23)12-9-7-5-6-8-11-14-22(27,28)16-35-37(29,30)31;;/h17-21H,2-16H2,1H3,(H,29,30,31)(H,32,33,34);;/q;2*+1/p-2/t17-,18+,19+,20+,21+;;/m0../s1

SMILES Code

CCCCCC[C@@H](Cl)[C@@H](Cl)[C@H](OS(=O)([O-])=O)[C@H](Cl)C[C@@H](Cl)CCCCCCCCC(Cl)(Cl)COS(=O)([O-])=O.[Na+].[Na+]

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 753.34 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: Moss Iii FR, Cabrera GE, McKenna GM, Salerno GJ, Shuken SR, Landry ML, Weiss TM, Burns NZ, Boxer SG. Halogenation-Dependent Effects of the Chlorosulfolipids of Ochromonas danica on Lipid Bilayers. ACS Chem Biol. 2020 Oct 9. doi: 10.1021/acschembio.0c00624. Epub ahead of print. PMID: 33035052. 2: Gropp C, Fischer S, Husch T, Trapp N, Carreira EM, Diederich F. Molecular Recognition and Cocrystallization of Methylated and Halogenated Fragments of Danicalipin A by Enantiopure Alleno-Acetylenic Cage Receptors. J Am Chem Soc. 2020 Mar 11;142(10):4749-4755. doi: 10.1021/jacs.9b13217. Epub 2020 Mar 1. PMID: 32114766. 3: Boshkow J, Fischer S, Bailey AM, Wolfrum S, Carreira EM. Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers. Chem Sci. 2017 Oct 1;8(10):6904-6910. doi: 10.1039/c7sc03124f. Epub 2017 Aug 9. PMID: 29147515; PMCID: PMC5632803. 4: Landry ML, Hu DX, McKenna GM, Burns NZ. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A. J Am Chem Soc. 2016 Apr 20;138(15):5150-8. doi: 10.1021/jacs.6b01643. Epub 2016 Apr 8. PMID: 27018981; PMCID: PMC4922634. 5: White AR, Duggan BM, Tsai SC, Vanderwal CD. The Alga Ochromonas danica Produces Bromosulfolipids. Org Lett. 2016 Mar 4;18(5):1124-7. doi: 10.1021/acs.orglett.6b00230. Epub 2016 Feb 18. PMID: 26889956; PMCID: PMC6020021. 6: Fischer S, Huwyler N, Wolfrum S, Carreira EM. Synthesis and Biological Evaluation of Bromo- and Fluorodanicalipin A. Angew Chem Int Ed Engl. 2016 Feb 12;55(7):2555-8. doi: 10.1002/anie.201510608. Epub 2016 Jan 14. PMID: 26840217. 7: Bailey AM, Wolfrum S, Carreira EM. Biological Investigations of (+)-Danicalipin A Enabled Through Synthesis. Angew Chem Int Ed Engl. 2016 Jan 11;55(2):639-43. doi: 10.1002/anie.201509082. Epub 2015 Nov 27. PMID: 26610732. 8: Chung WJ, Carlson JS, Vanderwal CD. General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form. J Org Chem. 2014 Mar 7;79(5):2226-41. doi: 10.1021/jo5000829. Epub 2014 Feb 13. PMID: 24494597; PMCID: PMC3954434. 9: Chung WJ, Vanderwal CD. Approaches to the chemical synthesis of the chlorosulfolipids. Acc Chem Res. 2014 Feb 18;47(2):718-28. doi: 10.1021/ar400246w. Epub 2014 Jan 8. PMID: 24400674; PMCID: PMC3949661. 10: Umezawa T, Shibata M, Kaneko K, Okino T, Matsuda F. Asymmetric total synthesis of danicalipin A and evaluation of biological activity. Org Lett. 2011 Mar 4;13(5):904-7. doi: 10.1021/ol102882a. Epub 2011 Feb 3. PMID: 21291262. 11: Yoshimitsu T, Nakatani R, Kobayashi A, Tanaka T. Asymmetric total synthesis of (+)-danicalipin A. Org Lett. 2011 Mar 4;13(5):908-11. doi: 10.1021/ol1029518. Epub 2011 Feb 2. PMID: 21288044. 12: Bedke DK, Shibuya GM, Pereira A, Gerwick WH, Haines TH, Vanderwal CD. Relative stereochemistry determination and synthesis of the major chlorosulfolipid from Ochromonas danica. J Am Chem Soc. 2009 Jun 10;131(22):7570-2. doi: 10.1021/ja902138w. PMID: 19445461.