5-PAHSA
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MedKoo CAT#: 412703

CAS#: 1481636-41-2

Description: 5-PAHSA is a FAHFA obtained by formal condensation of the carboxy group of palmitic acid with the hydroxy group of 5-hydroxystearic acid. It has a role as a human metabolite, an anti-inflammatory agent and a hypoglycemic agent. It is a FAHFA and a long-chain fatty acid. It derives from a hexadecanoic acid and an octadecanoic acid. It is a conjugate acid of a 5-PAHSA(1-).


Chemical Structure

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5-PAHSA
CAS# 1481636-41-2

Theoretical Analysis

MedKoo Cat#: 412703
Name: 5-PAHSA
CAS#: 1481636-41-2
Chemical Formula: C34H66O4
Exact Mass: 538.4961
Molecular Weight: 538.89
Elemental Analysis: C, 75.78; H, 12.35; O, 11.88

Price and Availability

Size Price Availability Quantity
1.0mg USD 257.0 2 Weeks
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Synonym: 5-PAHSA; 5-(palmitoyloxy)octadecanoic acid

IUPAC/Chemical Name: 5-(palmitoyloxy)octadecanoic acid

InChi Key: QBGKCWKQYJQHJX-UHFFFAOYSA-N

InChi Code: InChI=1S/C34H66O4/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-31-34(37)38-32(29-27-30-33(35)36)28-25-23-21-19-17-14-12-10-8-6-4-2/h32H,3-31H2,1-2H3,(H,35,36)

SMILES Code: CCCCCCCCCCCCCC(OC(CCCCCCCCCCCCCCC)=O)CCCC(O)=O

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 538.89 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: Paluchova V, Oseeva M, Brezinova M, Cajka T, Bardova K, Adamcova K, Zacek P, Brejchova K, Balas L, Chodounska H, Kudova E, Schreiber R, Zechner R, Durand T, Rossmeisl M, Abumrad NA, Kopecky J, Kuda O. Lipokine 5-PAHSA Is Regulated by Adipose Triglyceride Lipase and Primes Adipocytes for De Novo Lipogenesis in Mice. Diabetes. 2020 Mar;69(3):300-312. doi: 10.2337/db19-0494. Epub 2019 Dec 5. PMID: 31806624; PMCID: PMC7118252.

2: Pflimlin E, Bielohuby M, Korn M, Breitschopf K, Löhn M, Wohlfart P, Konkar A, Podeschwa M, Bärenz F, Pfenninger A, Schwahn U, Opatz T, Reimann M, Petry S, Tennagels N. Acute and Repeated Treatment with 5-PAHSA or 9-PAHSA Isomers Does Not Improve Glucose Control in Mice. Cell Metab. 2018 Aug 7;28(2):217-227.e13. doi: 10.1016/j.cmet.2018.05.028. Epub 2018 Jun 21. PMID: 29937376.

3: Wang YM, Liu HX, Fang NY. High Glucose Concentration Impairs 5-PAHSA Activity by Inhibiting AMP-Activated Protein Kinase Activation and Promoting Nuclear Factor-Kappa-B-Mediated Inflammation. Front Pharmacol. 2019 Jan 7;9:1491. doi: 10.3389/fphar.2018.01491. PMID: 30666198; PMCID: PMC6330329.

4: Syed I, Lee J, Moraes-Vieira PM, Donaldson CJ, Sontheimer A, Aryal P, Wellenstein K, Kolar MJ, Nelson AT, Siegel D, Mokrosinski J, Farooqi IS, Zhao JJ, Yore MM, Peroni OD, Saghatelian A, Kahn BB. Palmitic Acid Hydroxystearic Acids Activate GPR40, Which Is Involved in Their Beneficial Effects on Glucose Homeostasis. Cell Metab. 2018 Feb 6;27(2):419-427.e4. doi: 10.1016/j.cmet.2018.01.001. PMID: 29414687; PMCID: PMC5807007.

5: Bandak B, Yi L, Roper MG. Microfluidic-enabled quantitative measurements of insulin release dynamics from single islets of Langerhans in response to 5-palmitic acid hydroxy stearic acid. Lab Chip. 2018 Sep 11;18(18):2873-2882. doi: 10.1039/c8lc00624e. PMID: 30109329; PMCID: PMC6133761.

6: Brezinova M, Kuda O, Hansikova J, Rombaldova M, Balas L, Bardova K, Durand T, Rossmeisl M, Cerna M, Stranak Z, Kopecky J. Levels of palmitic acid ester of hydroxystearic acid (PAHSA) are reduced in the breast milk of obese mothers. Biochim Biophys Acta Mol Cell Biol Lipids. 2018 Feb;1863(2):126-131. doi: 10.1016/j.bbalip.2017.11.004. Epub 2017 Nov 14. PMID: 29154942.

7: Lee J, Moraes-Vieira PM, Castoldi A, Aryal P, Yee EU, Vickers C, Parnas O, Donaldson CJ, Saghatelian A, Kahn BB. Branched Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) Protect against Colitis by Regulating Gut Innate and Adaptive Immune Responses. J Biol Chem. 2016 Oct 14;291(42):22207-22217. doi: 10.1074/jbc.M115.703835. Epub 2016 Aug 29. PMID: 27573241; PMCID: PMC5064000.

8: Syed I, Rubin de Celis MF, Mohan JF, Moraes-Vieira PM, Vijayakumar A, Nelson AT, Siegel D, Saghatelian A, Mathis D, Kahn BB. PAHSAs attenuate immune responses and promote β cell survival in autoimmune diabetic mice. J Clin Invest. 2019 Aug 5;129(9):3717-3731. doi: 10.1172/JCI122445. PMID: 31380811; PMCID: PMC6715391.

9: Brejchova K, Balas L, Paluchova V, Brezinova M, Durand T, Kuda O. Understanding FAHFAs: From structure to metabolic regulation. Prog Lipid Res. 2020 Jul;79:101053. doi: 10.1016/j.plipres.2020.101053. Epub 2020 Jul 29. PMID: 32735891.

10: Zhu QF, Yan JW, Gao Y, Zhang JW, Yuan BF, Feng YQ. Highly sensitive determination of fatty acid esters of hydroxyl fatty acids by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Sep 1;1061-1062:34-40. doi: 10.1016/j.jchromb.2017.06.045. Epub 2017 Jun 27. PMID: 28704723.

5-PAHSA

1.0mg / USD 257.0