Sapienic acid | CAS#17004-51-2

MedKoo Cat#: 527995 | Name: Sapienic acid

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Description:

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

Sapienic acid is a fatty acid that is a major component of human sebum. Sapienic acid is a sebum fatty acid that is unique to humans (from whose scientific name it takes the root sapiens). The equivalent fatty acid in mouse sebum is palmitoleic acid. Sapienic acid salts, esters, anion, and conjugate base are known as sapienates. Deficient production of sapienic acid has been implicated in the development of atopic dermatitis, and sapienic acid has potent antibacterial activity against pathogens like Staphylococcus aureus.

Chemical Structure

Sapienic acid

CAS#17004-51-2

Theoretical Analysis

MedKoo Cat#: 527995

Name: Sapienic acid

CAS#: 17004-51-2

Chemical Formula: C16H30O2

Exact Mass: 254.2246

Molecular Weight: 254.41

Elemental Analysis: C, 75.54; H, 11.89; O, 12.58

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 550.00	2 Weeks
25mg	USD 950.00	2 Weeks

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Related CAS #

No Data

Synonym

Sapienic acid

IUPAC/Chemical Name

6-Hexadecenoic acid, (6Z)-

InChi Key

NNNVXFKZMRGJPM-KHPPLWFESA-N

InChi Code

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h10-11H,2-9,12-15H2,1H3,(H,17,18)/b11-10-

SMILES Code

CCCCCCCCC/C=C\CCCCC(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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 254.41 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.

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: Kengmo Tchoupa A, Elsherbini AMA, Camus J, Fu X, Hu X, Ghaneme O, Seibert L, Lebtig M, Böcker MA, Horlbeck A, Lambidis SP, Schittek B, Kretschmer D, Lämmerhofer M, Peschel A. Lipase-mediated detoxification of host-derived antimicrobial fatty acids by Staphylococcus aureus. Commun Biol. 2024 May 15;7(1):572. doi: 10.1038/s42003-024-06278-3. PMID: 38750133; PMCID: PMC11096360. 2: Kothapalli KSD, Park HG, Kothapalli NSL, Brenna JT. FADS2 function at the major cancer hotspot 11q13 locus alters fatty acid metabolism in cancer. Prog Lipid Res. 2023 Nov;92:101242. doi: 10.1016/j.plipres.2023.101242. Epub 2023 Aug 18. PMID: 37597812. 3: Bermúdez MA, Pereira L, Fraile C, Valerio L, Balboa MA, Balsinde J. Roles of Palmitoleic Acid and Its Positional Isomers, Hypogeic and Sapienic Acids, in Inflammation, Metabolic Diseases and Cancer. Cells. 2022 Jul 8;11(14):2146. doi: 10.3390/cells11142146. PMID: 35883589; PMCID: PMC9319324. 4: Gan L, Park K, Chai J, Updike EM, Kim H, Voshall A, Behera S, Yu XH, Cai Y, Zhang C, Wilson MA, Mower JP, Moriyama EN, Zhang C, Kaewsuwan S, Liu Q, Shanklin J, Cahoon EB. Divergent evolution of extreme production of variant plant monounsaturated fatty acids. Proc Natl Acad Sci U S A. 2022 Jul 26;119(30):e2201160119. doi: 10.1073/pnas.2201160119. Epub 2022 Jul 22. PMID: 35867834; PMCID: PMC9335243. 5: Küçüksayan E, Sansone A, Chatgilialoglu C, Ozben T, Tekeli D, Talibova G, Ferreri C. Sapienic Acid Metabolism Influences Membrane Plasticity and Protein Signaling in Breast Cancer Cell Lines. Cells. 2022 Jan 11;11(2):225. doi: 10.3390/cells11020225. PMID: 35053341; PMCID: PMC8773705. 6: Wallis CM, Lawrence DP, Travadon R, Baumgartner K. Characterization of grapevine fungal canker pathogens Fatty Acid Methyl Ester (FAME) profiles. Mycologia. 2022 Jan-Feb;114(1):203-213. doi: 10.1080/00275514.2021.1983396. Epub 2021 Dec 10. PMID: 34890530. 7: Kuiack RC, Veldhuizen RAW, McGavin MJ. Novel Functions and Signaling Specificity for the GraS Sensor Kinase of Staphylococcus aureus in Response to Acidic pH. J Bacteriol. 2020 Oct 22;202(22):e00219-20. doi: 10.1128/JB.00219-20. PMID: 32868405; PMCID: PMC7585063. 8: Ferreri C, Sansone A, Ferreri R, Amézaga J, Tueros I. Fatty Acids and Membrane Lipidomics in Oncology: A Cross-Road of Nutritional, Signaling and Metabolic Pathways. Metabolites. 2020 Aug 25;10(9):345. doi: 10.3390/metabo10090345. PMID: 32854444; PMCID: PMC7570129. 9: Tiwari KB, Gatto C, Wilkinson BJ. Plasticity of Coagulase-Negative Staphylococcal Membrane Fatty Acid Composition and Implications for Responses to Antimicrobial Agents. Antibiotics (Basel). 2020 Apr 28;9(5):214. doi: 10.3390/antibiotics9050214. PMID: 32354049; PMCID: PMC7277709. 10: Ferreri C, Sansone A, Buratta S, Urbanelli L, Costanzi E, Emiliani C, Chatgilialoglu C. The n-10 Fatty Acids Family in the Lipidome of Human Prostatic Adenocarcinoma Cell Membranes and Extracellular Vesicles. Cancers (Basel). 2020 Apr 7;12(4):900. doi: 10.3390/cancers12040900. PMID: 32272739; PMCID: PMC7226157. 11: Subramanian C, Frank MW, Batte JL, Whaley SG, Rock CO. Oleate hydratase from Staphylococcus aureus protects against palmitoleic acid, the major antimicrobial fatty acid produced by mammalian skin. J Biol Chem. 2019 Jun 7;294(23):9285-9294. doi: 10.1074/jbc.RA119.008439. Epub 2019 Apr 24. PMID: 31018965; PMCID: PMC6556589. 12: Scanferlato R, Bortolotti M, Sansone A, Chatgilialoglu C, Polito L, De Spirito M, Maulucci G, Bolognesi A, Ferreri C. Hexadecenoic Fatty Acid Positional Isomers and De Novo PUFA Synthesis in Colon Cancer Cells. Int J Mol Sci. 2019 Feb 15;20(4):832. doi: 10.3390/ijms20040832. PMID: 30769921; PMCID: PMC6412212. 13: Wertz PW. Lipids and the Permeability and Antimicrobial Barriers of the Skin. J Lipids. 2018 Sep 2;2018:5954034. doi: 10.1155/2018/5954034. PMID: 30245886; PMCID: PMC6139190. 14: Bukowiecka-Matusiak M, Burzynska-Pedziwiatr I, Sansone A, Malachowska B, Zurawska-Klis M, Ferreri C, Chatgilialoglu C, Ochedalski T, Cypryk K, Wozniak LA. Lipid profile changes in erythrocyte membranes of women with diagnosed GDM. PLoS One. 2018 Sep 14;13(9):e0203799. doi: 10.1371/journal.pone.0203799. PMID: 30216387; PMCID: PMC6138398. 15: Astudillo AM, Meana C, Guijas C, Pereira L, Lebrero P, Balboa MA, Balsinde J. Occurrence and biological activity of palmitoleic acid isomers in phagocytic cells. J Lipid Res. 2018 Feb;59(2):237-249. doi: 10.1194/jlr.M079145. Epub 2017 Nov 21. PMID: 29167413; PMCID: PMC5794419. 16: Moran JC, Alorabi JA, Horsburgh MJ. Comparative Transcriptomics Reveals Discrete Survival Responses of S. aureus and S. epidermidis to Sapienic Acid. Front Microbiol. 2017 Jan 25;8:33. doi: 10.3389/fmicb.2017.00033. PMID: 28179897; PMCID: PMC5263133. 17: Ferreri C, Masi A, Sansone A, Giacometti G, Larocca AV, Menounou G, Scanferlato R, Tortorella S, Rota D, Conti M, Deplano S, Louka M, Maranini AR, Salati A, Sunda V, Chatgilialoglu C. Fatty Acids in Membranes as Homeostatic, Metabolic and Nutritional Biomarkers: Recent Advancements in Analytics and Diagnostics. Diagnostics (Basel). 2016 Dec 22;7(1):1. doi: 10.3390/diagnostics7010001. PMID: 28025506; PMCID: PMC5373010. 18: Pleik S, Spengler B, Schäfer T, Urbach D, Luhn S, Kirsch D. Fatty Acid Structure and Degradation Analysis in Fingerprint Residues. J Am Soc Mass Spectrom. 2016 Sep;27(9):1565-74. doi: 10.1007/s13361-016-1429-6. Epub 2016 Jun 20. PMID: 27324649. 19: Sansone A, Tolika E, Louka M, Sunda V, Deplano S, Melchiorre M, Anagnostopoulos D, Chatgilialoglu C, Formisano C, Di Micco R, Faraone Mennella MR, Ferreri C. Hexadecenoic Fatty Acid Isomers in Human Blood Lipids and Their Relevance for the Interpretation of Lipidomic Profiles. PLoS One. 2016 Apr 5;11(4):e0152378. doi: 10.1371/journal.pone.0152378. PMID: 27045677; PMCID: PMC4821613. 20: Al-Dhabi NA, Valan Arasu M. Quantification of Phytochemicals from Commercial Spirulina Products and Their Antioxidant Activities. Evid Based Complement Alternat Med. 2016;2016:7631864. doi: 10.1155/2016/7631864. Epub 2016 Jan 4. PMID: 26933442; PMCID: PMC4737012.