Danicalipin A

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

MedKoo CAT#: 463320

CAS#: unknown

Description: 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

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Danicalipin A
CAS# unknown

Theoretical Analysis

MedKoo Cat#: 463320
Name: Danicalipin A
CAS#: unknown
Chemical Formula: C22H38Cl6Na2O8S2
Exact Mass: 749.9935
Molecular Weight: 753.3375
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 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.

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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

Preparing Stock Solutions

The following data is based on the product molecular weight 753.3375 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: 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.