Oleic acid | CAS#112-80-1 | fatty acid

MedKoo Cat#: 341038 | Name: Oleic acid

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Description:

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

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils.

Chemical Structure

Oleic acid

CAS#112-80-1

Theoretical Analysis

MedKoo Cat#: 341038

Name: Oleic acid

CAS#: 112-80-1

Chemical Formula: C18H34O2

Exact Mass: 282.2559

Molecular Weight: 282.47

Elemental Analysis: C, 76.54; H, 12.13; O, 11.33

Price and Availability

Size	Price	Availability	Quantity
5g	USD 350.00	2 Weeks

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Related CAS #

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Synonym

Oleic acid; D 100; cis-9-Octadecenoic acid; oleate; cis-Oleic acid; NSC-9856; NSC9856; NSC 9856

IUPAC/Chemical Name

9-Octadecenoic acid (9Z)-

InChi Key

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

InChi Code

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

SMILES Code

C(CC\C=C/CCCCCCCC)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

>2 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oleic acid is a Na+/K+ ATPase activator.

In vitro activity:

This study reported that AMP-activated protein kinase (AMPK) was obviously activated in highly aggressive carcinoma cell lines treated by oleic acid, including gastric carcinoma HGC-27 and breast carcinoma MDA-MB-231 cell lines. AMPK enhanced the rates of fatty acid oxidation and ATP production and thus significantly promoted cancer growth and migration under serum deprivation. Inactivation of AMPK attenuated these activities of oleic acid. Oleic acid inhibited cancer cell growth and survival in low metastatic carcinoma cells, such as gastric carcinoma SGC7901 and breast carcinoma MCF-7 cell lines. Reference: PLoS One. 2014 May 13;9(5):e97330. https://pubmed.ncbi.nlm.nih.gov/24823908/

In vivo activity:

The present study is aimed to explore whether oleic acid can afford protection to rat gastric tissue when challenged with adrenaline. Pre-treatment of rats with oleic acid dose-dependently protected against these gastric injuries induced by adrenaline indicating the potentiality of oleic acid in protecting against adrenaline induced gastric injury in male albino rats where antioxidant mechanisms appear to play a pivotal role in mediating such protection. Reference: Heliyon. 2021 Mar 17;7(3):e06476. https://pubmed.ncbi.nlm.nih.gov/33768175/

	Solvent	mg/mL	mM
Solubility
	DMSO	62.5	221.26
	Ethanol	100.0	354.02

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 282.47 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:

1. Banerjee A, Dey T, Majumder R, Bhattacharya T, Dey S, Bandyopadhyay D, Chattopadhyay A. Oleic acid prevents erythrocyte death by preserving haemoglobin and erythrocyte membrane proteins. Free Radic Biol Med. 2023 Mar 23;202:17-33. doi: 10.1016/j.freeradbiomed.2023.03.019. Epub ahead of print. PMID: 36965537. 2. Li S, Zhou T, Li C, Dai Z, Che D, Yao Y, Li L, Ma J, Yang X, Gao G. High metastaticgastric and breast cancer cells consume oleic acid in an AMPK dependent manner. PLoS One. 2014 May 13;9(5):e97330. doi: 10.1371/journal.pone.0097330. PMID: 24823908; PMCID: PMC4019637. 3. Kim SH, Hong JH, Yang WK, Kim HJ, An HJ, Lee YC. Cryptotympana pustulata Extract and Its Main Active Component, Oleic Acid, Inhibit Ovalbumin-Induced Allergic Airway Inflammation through Inhibition of Th2/GATA-3 and Interleukin-17/RORγt Signaling Pathways in Asthmatic Mice. Molecules. 2021 Mar 25;26(7):1854. doi: 10.3390/molecules26071854. PMID: 33806085; PMCID: PMC8037444. 4. Mishra S, Chattopadhyay A, Naaz S, Banerjee A, Ghosh AK, Pal PK, Bhattacharya T, Das A, Chattopadhyay S, Bandyopadhyay D. Oleic acid as a restorative agent in alleviating adrenaline induced altered morphofunctional milieu of gastric tissue and mitochondria. Heliyon. 2021 Mar 17;7(3):e06476. doi: 10.1016/j.heliyon.2021.e06476. PMID: 33768175; PMCID: PMC7980076.

In vitro protocol:

In vivo protocol:

1. Kim SH, Hong JH, Yang WK, Kim HJ, An HJ, Lee YC. Cryptotympana pustulata Extract and Its Main Active Component, Oleic Acid, Inhibit Ovalbumin-Induced Allergic Airway Inflammation through Inhibition of Th2/GATA-3 and Interleukin-17/RORγt Signaling Pathways in Asthmatic Mice. Molecules. 2021 Mar 25;26(7):1854. doi: 10.3390/molecules26071854. PMID: 33806085; PMCID: PMC8037444. 2. Mishra S, Chattopadhyay A, Naaz S, Banerjee A, Ghosh AK, Pal PK, Bhattacharya T, Das A, Chattopadhyay S, Bandyopadhyay D. Oleic acid as a restorative agent in alleviating adrenaline induced altered morphofunctional milieu of gastric tissue and mitochondria. Heliyon. 2021 Mar 17;7(3):e06476. doi: 10.1016/j.heliyon.2021.e06476. PMID: 33768175; PMCID: PMC7980076.

1: Rufino MOA, Salles MSV, Negrão JA, Daniel JLP, de Lima LS, De Marchi FE, Roma Júnior LC, Dos Santos GT. Energy balance in grazing Jersey cows in early lactation supplemented with peanut and sunflower oils. Trop Anim Health Prod. 2018 Feb 9. doi: 10.1007/s11250-018-1531-9. [Epub ahead of print] PubMed PMID: 29427245. 2: Spreafico F, Sales RC, Gil-Zamorano J, Medeiros PDC, Latasa MJ, Lima MR, de Souza SAL, Martin-Hernández R, Gómez-Coronado D, Iglesias-Gutierrez E, Mantilla-Escalante DC, das Graças Tavares do Carmo M, Dávalos A. Dietary supplementation with hybrid palm oil alters liver function in the common Marmoset. Sci Rep. 2018 Feb 9;8(1):2765. doi: 10.1038/s41598-018-21151-0. PubMed PMID: 29426919. 3: Dutta L, Mukherjee B, Chakraborty T, Das MK, Mondal L, Bhattacharya S, Gaonkar RH, Debnath MC. Lipid-based nanocarrier efficiently delivers highly water soluble drug across the blood-brain barrier into brain. Drug Deliv. 2018 Nov;25(1):504-516. doi: 10.1080/10717544.2018.1435749. PubMed PMID: 29426257. 4: Zhang Y, Han F, Dai Q, Tang J. Magnetic properties and photovoltaic applications of ZnO:Mn nanocrystals. J Colloid Interface Sci. 2018 Feb 2;517:194-203. doi: 10.1016/j.jcis.2018.02.002. [Epub ahead of print] PubMed PMID: 29425956. 5: Lopes LL, Rocha DMUP, Silva AD, Peluzio MDCG, Bressan J, Hermsdorff HHM. Postprandial Lipid Response to High-Saturated and High-Monounsaturated Fat Meals in Normal-Weight or Overweight Women. J Am Coll Nutr. 2018 Feb 9:1-8. doi: 10.1080/07315724.2017.1399835. [Epub ahead of print] PubMed PMID: 29425478. 6: Shin S, Ajuwon KM. Divergent Response of Murine and Porcine Adipocytes to Stimulation of Browning Genes by 18-Carbon Polyunsaturated Fatty Acids and Beta-Receptor Agonists. Lipids. 2018 Feb 9. doi: 10.1002/lipd.12010. [Epub ahead of print] PubMed PMID: 29424439. 7: Alencar DB, Diniz JC, Rocha SAS, Pires-Cavalcante KMS, Lima RL, Sousa KC, Freitas JO, Bezerra RM, Baracho BM, Sampaio AH, Viana FA, Saker-Sampaio S. Fatty acid composition from the marine red algae Pterocladiella capillacea (S. G. Gmelin) Santelices & Hommersand 1997 and Osmundaria obtusiloba (C. Agardh) R. E. Norris 1991 and its antioxidant activity. An Acad Bras Cienc. 2018 Feb 1:0. doi: 10.1590/0001-3765201820160315. [Epub ahead of print] PubMed PMID: 29424393. 8: Rahrovani F, Javanbakht MH, Ghaedi E, Mohammadi H, Ehsani AH, Esrafili A, Djalali M. Erythrocyte Membrane Unsaturated (Mono and Poly) Fatty Acids Profile in Newly Diagnosed Basal Cell Carcinoma Patients. Clin Nutr Res. 2018 Jan;7(1):21-30. doi: 10.7762/cnr.2018.7.1.21. Epub 2018 Jan 24. PubMed PMID: 29423386; PubMed Central PMCID: PMC5796920. 9: Liu L, Chen J, Lim PE, Wei D. Enhanced single cell oil production by mixed culture of Chlorella pyrenoidosa and Rhodotorula glutinis using cassava bagasse hydrolysate as carbon source. Bioresour Technol. 2018 Feb 2;255:140-148. doi: 10.1016/j.biortech.2018.01.114. [Epub ahead of print] PubMed PMID: 29414159. 10: Chatterjee S, Mohan SV. Microbial lipid production by Cryptococcus curvatus from vegetable waste hydrolysate. Bioresour Technol. 2018 Jan 31;254:284-289. doi: 10.1016/j.biortech.2018.01.079. [Epub ahead of print] PubMed PMID: 29413935. 11: Park HG, Engel MG, Vogt-Lowell K, Lawrence P, Kothapalli KS, Brenna JT. The role of fatty acid desaturase (FADS) genes in oleic acid metabolism: FADS1 Δ7 desaturates 11-20:1 to 7,11-20:2. Prostaglandins Leukot Essent Fatty Acids. 2018 Jan;128:21-25. doi: 10.1016/j.plefa.2017.11.004. Epub 2017 Nov 21. PubMed PMID: 29413358; PubMed Central PMCID: PMC5806126. 12: Caleja C, Barros L, Barreira JCM, Ciric A, Sokovic M, Calhelha RC, Beatriz M, Oliveira PP, Ferreira ICFR. Suitability of lemon balm (Melissa officinalis L.) extract rich in rosmarinic acid as a potential enhancer of functional properties in cupcakes. Food Chem. 2018 Jun 1;250:67-74. doi: 10.1016/j.foodchem.2018.01.034. Epub 2018 Jan 4. PubMed PMID: 29412929. 13: Tabandeh M, Salman AA, Goh EW, Heidelberg T, Hussen RSD. Renewable resources-based approach to biantennary glycolipids. Chem Phys Lipids. 2018 Jan 31;212:111-119. doi: 10.1016/j.chemphyslip.2018.01.011. [Epub ahead of print] PubMed PMID: 29409839. 14: Raja Gopal Reddy M, Mullapudi Venkata S, Putcha UK, Jeyakumar SM. Vitamin A deficiency induces endoplasmic reticulum stress and apoptosis in pancreatic islet cells: Implications of stearoyl-CoA desaturase 1-mediated oleic acid synthesis. Exp Cell Res. 2018 Feb 1. pii: S0014-4827(18)30049-1. doi: 10.1016/j.yexcr.2018.01.040. [Epub ahead of print] PubMed PMID: 29409806. 15: Padmajan Sasikala S, Mahesh KV, Prabhakaran P, Peer Mohammed A, Ananthakumar S. Multiwall carbon nanotube reinforced teflon fibrils for oil spill clean up and its effective recycling as textile dye sorbent. J Environ Manage. 2018 Feb 2;211:198-205. doi: 10.1016/j.jenvman.2018.01.011. [Epub ahead of print] PubMed PMID: 29408067. 16: Xia Q, Wang L, Li Y. Exploring high hydrostatic pressure-mediated germination to enhance functionality and quality attributes of wholegrain brown rice. Food Chem. 2018 May 30;249:104-110. doi: 10.1016/j.foodchem.2018.01.007. Epub 2018 Jan 2. PubMed PMID: 29407912. 17: Celeste Dias M, Pinto DCGA, Correia C, Moutinho-Pereira J, Oliveira H, Freitas H, Silva AMS, Santos C. UV-B radiation modulates physiology and lipophilic metabolite profile in Olea europaea. J Plant Physiol. 2018 Jan 29;222:39-50. doi: 10.1016/j.jplph.2018.01.004. [Epub ahead of print] PubMed PMID: 29407548. 18: Zhang X, Ji R, Sun H, Peng J, Ma X, Wang C, Fu Y, Bao L, Jin Y. Scutellarin ameliorates nonalcoholic fatty liver disease through the PPARγ/PGC-1α-Nrf2 pathway. Free Radic Res. 2018 Feb 5:1-14. doi: 10.1080/10715762.2017.1422602. [Epub ahead of print] PubMed PMID: 29400110. 19: Elkady WM, Ibrahim EA, Gonaid MH, El Baz FK. Chemical Profile and Biological Activity of Casimiroa Edulis Non-Edible Fruit`s Parts. Adv Pharm Bull. 2017 Dec;7(4):655-660. doi: 10.15171/apb.2017.079. Epub 2017 Dec 31. PubMed PMID: 29399557; PubMed Central PMCID: PMC5788222. 20: Silva LCC, Bueno RD, da Matta LB, Pereira PHS, Mayrink DB, Piovesan ND, Sediyama CS, Fontes EPB, Cardinal AJ, Dal-Bianco M. Characterization of a new GmFAD3A allele in Brazilian CS303TNKCA soybean cultivar. Theor Appl Genet. 2018 Feb 3. doi: 10.1007/s00122-018-3061-2. [Epub ahead of print] PubMed PMID: 29397403.