Minerval | CAS# 56472-29-8 | Biochemical

MedKoo Cat#: 529606 | Name: Minerval

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Description:

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

Minerval, also known as 2-OHOA, is a fatty acid amide hydrolase inhibitor, protein kinase C activator, and a sphingomyelin synthase activator with antineoplastic activity.

Chemical Structure

Minerval

CAS#56472-29-8

Theoretical Analysis

MedKoo Cat#: 529606

Name: Minerval

CAS#: 56472-29-8

Chemical Formula: C18H34O3

Exact Mass: 298.2508

Molecular Weight: 298.47

Elemental Analysis: C, 72.44; H, 11.48; O, 16.08

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 585.00	2 weeks
25mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

2-OHOA; 2OHOA; 2 OHOA; Idroxioleic acid

IUPAC/Chemical Name

(Z)-2-hydroxyoctadec-9-enoic acid

InChi Key

JBSOOFITVPOOSY-KTKRTIGZSA-N

InChi Code

InChI=1S/C18H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h9-10,17,19H,2-8,11-16H2,1H3,(H,20,21)/b10-9-

SMILES Code

CCCCCCCC/C=C\CCCCCCC(O)C(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:

(Rac)-Idroxioleic acid (2-Hydroxyoleic acid) is a synthetic oleic acid (OA) derivative that binds to the plasma membrane and alters lipid organization. (Rac)-Idroxioleic acid has anti-tumor effect.

In vitro activity:

Minerval also acts, selectively in cancer cell lines, as an ATP depleting uncoupler of mitochondrial oxidative phosphorylation (OxPhos). As a function of its exposure time, Minerval compromised the capacity of glioblastoma U87-MG cells to compensate for aberrant respiration by up-modulation of glycolysis. Additionally, compared with other OxPhos inhibitors, Minerval uniquely induced ER stress in cancer cell lines. Reference: Biosci Rep. 2019 Jan 18;39(1):BSR20181661. https://pubmed.ncbi.nlm.nih.gov/30602451/

In vivo activity:

Minerval treatments markedly and significantly inhibited tumour growth in nude mice infected with Jurkat cells. Tumours from control (untreated) mice increased 431 ± 24% between days 10 and 31 after tumour implantation, whereas the average increase in tumour volume of Minerval-treated animals was 24 ± 16% (three out of eight animals showing tumour reductions) (Fig. 5). Reference: J Cell Mol Med. 2010 Mar;14(3):659-70. https://pubmed.ncbi.nlm.nih.gov/19413889/

Preparing Stock Solutions

The following data is based on the product molecular weight 298.47 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. Massalha W, Markovits M, Pichinuk E, Feinstein-Rotkopf Y, Tarshish M, Mishra K, Llado V, Weil M, Escriba PV, Kakhlon O. Minerval (2-hydroxyoleic acid) causes cancer cell selective toxicity by uncoupling oxidative phosphorylation and compromising bioenergetic compensation capacity. Biosci Rep. 2019 Jan 18;39(1):BSR20181661. doi: 10.1042/BSR20181661. PMID: 30602451; PMCID: PMC6340956. 2. Torgersen ML, Klokk TI, Kavaliauskiene S, Klose C, Simons K, Skotland T, Sandvig K. The anti-tumor drug 2-hydroxyoleic acid (Minerval) stimulates signaling and retrograde transport. Oncotarget. 2016 Dec 27;7(52):86871-86888. doi: 10.18632/oncotarget.13508. PMID: 27894086; PMCID: PMC5349960. 3. Llado V, Gutierrez A, Martínez J, Casas J, Terés S, Higuera M, Galmés A, Saus C, Besalduch J, Busquets X, Escribá PV. Minerval induces apoptosis in Jurkat and other cancer cells. J Cell Mol Med. 2010 Mar;14(3):659-70. doi: 10.1111/j.1582-4934.2008.00625.x. Epub 2008 Dec 24. PMID: 19413889; PMCID: PMC3823464. 4. Martínez J, Vögler O, Casas J, Barceló F, Alemany R, Prades J, Nagy T, Baamonde C, Kasprzyk PG, Terés S, Saus C, Escribá PV. Membrane structure modulation, protein kinase C alpha activation, and anticancer activity of minerval. Mol Pharmacol. 2005 Feb;67(2):531-40. doi: 10.1124/mol.104.000778. Epub 2004 Nov 5. PMID: 15531732.

In vitro protocol:

In vivo protocol:

1. Llado V, Gutierrez A, Martínez J, Casas J, Terés S, Higuera M, Galmés A, Saus C, Besalduch J, Busquets X, Escribá PV. Minerval induces apoptosis in Jurkat and other cancer cells. J Cell Mol Med. 2010 Mar;14(3):659-70. doi: 10.1111/j.1582-4934.2008.00625.x. Epub 2008 Dec 24. PMID: 19413889; PMCID: PMC3823464. 2. Martínez J, Vögler O, Casas J, Barceló F, Alemany R, Prades J, Nagy T, Baamonde C, Kasprzyk PG, Terés S, Saus C, Escribá PV. Membrane structure modulation, protein kinase C alpha activation, and anticancer activity of minerval. Mol Pharmacol. 2005 Feb;67(2):531-40. doi: 10.1124/mol.104.000778. Epub 2004 Nov 5. PMID: 15531732.

1: Llado V, Gutierrez A, Martínez J, Casas J, Terés S, Higuera M, Galmés A, Saus C, Besalduch J, Busquets X, Escribá PV. Minerval induces apoptosis in Jurkat and other cancer cells. J Cell Mol Med. 2010 Mar;14(3):659-70. doi: 10.1111/j.1582-4934.2008.00625.x. PubMed PMID: 19413889; PubMed Central PMCID: PMC3823464. 2: Martínez J, Gutiérrez A, Casas J, Lladó V, López-Bellan A, Besalduch J, Dopazo A, Escribá PV. The repression of E2F-1 is critical for the activity of Minerval against cancer. J Pharmacol Exp Ther. 2005 Oct;315(1):466-74. PubMed PMID: 16027227. 3: Martínez J, Vögler O, Casas J, Barceló F, Alemany R, Prades J, Nagy T, Baamonde C, Kasprzyk PG, Terés S, Saus C, Escribá PV. Membrane structure modulation, protein kinase C alpha activation, and anticancer activity of minerval. Mol Pharmacol. 2005 Feb;67(2):531-40. PubMed PMID: 15531732. 4: Torgersen ML, Klokk TI, Kavaliauskiene S, Klose C, Simons K, Skotland T, Sandvig K. The anti-tumor drug 2-hydroxyoleic acid (Minerval) stimulates signaling and retrograde transport. Oncotarget. 2016 Dec 27;7(52):86871-86888. doi: 10.18632/oncotarget.13508. PubMed PMID: 27894086. 5: Lladó V, Terés S, Higuera M, Alvarez R, Noguera-Salva MA, Halver JE, Escribá PV, Busquets X. Pivotal role of dihydrofolate reductase knockdown in the anticancer activity of 2-hydroxyoleic acid. Proc Natl Acad Sci U S A. 2009 Aug 18;106(33):13754-8. doi: 10.1073/pnas.0907300106. PubMed PMID: 19666584; PubMed Central PMCID: PMC2720411. 6: Lladó V, López DJ, Ibarguren M, Alonso M, Soriano JB, Escribá PV, Busquets X. Regulation of the cancer cell membrane lipid composition by NaCHOleate: effects on cell signaling and therapeutical relevance in glioma. Biochim Biophys Acta. 2014 Jun;1838(6):1619-27. doi: 10.1016/j.bbamem.2014.01.027. Review. PubMed PMID: 24525074.