9-PAHSA | CAS# 1481636-31-0 | human metabolite, hypoglycemic agent, anti-inflammatory agent

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

MedKoo CAT#: 412702

CAS#: 1481636-31-0

Description: 9-PAHSA is a FAHFA (fatty acid ester of a hydroxy fatty acid) obtained by formal condensation of the carboxy group of palmitic acid with the hydroxy group of 9-hydroxyoctadecanoic acid (9-hydroxystearic acid). It has a role as a human metabolite, a hypoglycemic agent and an anti-inflammatory agent.

Chemical Structure

9-PAHSA

CAS# 1481636-31-0

Instruction

Theoretical Analysis

MedKoo Cat#: 412702
Name: 9-PAHSA
CAS#: 1481636-31-0
Chemical Formula: C34H66O4
Exact Mass: 538.50
Molecular Weight: 538.890
Elemental Analysis: C, 75.78; H, 12.35; O, 11.88

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 9-PAHSA; 9-(palmitoyloxy)octadecanoic acid

IUPAC/Chemical Name: 9-(palmitoyloxy)octadecanoic acid

InChi Key:

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

SMILES Code: CCCCCCCCCC(OC(CCCCCCCCCCCCCCC)=O)CCCCCCCC(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

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Wang YM, Liu HX, Fang NY. 9-PAHSA promotes browning of white fat via activating G-protein-coupled receptor 120 and inhibiting lipopolysaccharide / NF-kappa B pathway. Biochem Biophys Res Commun. 2018 Nov 17;506(1):153-160. doi: 10.1016/j.bbrc.2018.09.050. Epub 2018 Oct 16. PMID: 30340828.

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: Nelson AT, Kolar MJ, Chu Q, Syed I, Kahn BB, Saghatelian A, Siegel D. Stereochemistry of Endogenous Palmitic Acid Ester of 9-Hydroxystearic Acid and Relevance of Absolute Configuration to Regulation. J Am Chem Soc. 2017 Apr 5;139(13):4943-4947. doi: 10.1021/jacs.7b01269. Epub 2017 Mar 28. PMID: 28350171; PMCID: PMC5568760.

4: 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.

5: 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.

6: Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB. Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. PMID: 25303528; PMCID: PMC4260972.

7: Wang H, Chang T, Konduri S, Huang J, Saghatelian A, Siegel D. Synthesis of chemically edited derivatives of the endogenous regulator of inflammation 9-PAHSA. J Antibiot (Tokyo). 2019 Jun;72(6):498-506. doi: 10.1038/s41429-019-0180-1. Epub 2019 Apr 15. PMID: 30988370; PMCID: PMC6784544.

8: Schultz Moreira AR, Rüschenbaum S, Schefczyk S, Hendgen-Cotta U, Rassaf T, Broering R, Hardtke-Wolenski M, Buitrago-Molina LE. 9-PAHSA Prevents Mitochondrial Dysfunction and Increases the Viability of Steatotic Hepatocytes. Int J Mol Sci. 2020 Nov 5;21(21):8279. doi: 10.3390/ijms21218279. PMID: 33167328; PMCID: PMC7663845.

9: Wen XH, Guo QL, Guo JC. Effect of 9 - PAHSA on cognitive dysfunction in diabetic mice and its possible mechanism. Biochem Biophys Res Commun. 2020 Apr 9;524(3):525-532. doi: 10.1016/j.bbrc.2020.01.071. Epub 2020 Feb 1. PMID: 32014256.

10: Vijayakumar A, Aryal P, Wen J, Syed I, Vazirani RP, Moraes-Vieira PM, Camporez JP, Gallop MR, Perry RJ, Peroni OD, Shulman GI, Saghatelian A, McGraw TE, Kahn BB. Absence of Carbohydrate Response Element Binding Protein in Adipocytes Causes Systemic Insulin Resistance and Impairs Glucose Transport. Cell Rep. 2017 Oct 24;21(4):1021-1035. doi: 10.1016/j.celrep.2017.09.091. PMID: 29069585; PMCID: PMC5771491.

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