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

MedKoo CAT#: 574585

CAS#: 221632-26-4

Description: OBAA is a potent inhibitor of phospholipase A2 that reduces bronchospasm in guinea pigs in vivo.


Chemical Structure

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OBAA
CAS# 221632-26-4

Theoretical Analysis

MedKoo Cat#: 574585
Name: OBAA
CAS#: 221632-26-4
Chemical Formula: C28H44O3
Exact Mass: 428.33
Molecular Weight: 428.657
Elemental Analysis: C, 78.46; H, 10.35; O, 11.20

Price and Availability

Size Price Availability Quantity
10mg USD 325 2 Weeks
50mg USD 1050 2 Weeks
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Synonym: OBAA

IUPAC/Chemical Name: 4-(4-Octadecylphenyl)-4-oxobutenoic acid

InChi Key: ZBESASFHIWDSCJ-WCWDXBQESA-N

InChi Code: InChI=1S/C28H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-25-19-21-26(22-20-25)27(29)23-24-28(30)31/h19-24H,2-18H2,1H3,(H,30,31)/b24-23+

SMILES Code: O=C(O)/C=C/C(C1=CC=C(CCCCCCCCCCCCCCCCCC)C=C1)=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:

Product Data:
Biological target: (2E)-OBAA is a potent phospholipase A2 (PLA2) inhibitor, with an IC50 of 70 nM.
In vitro activity: The present study examined whether LPC activates phospholipase A2 (PLA2) and whether the activation of PLA2 is responsible for the LPC-induced cell damage in isolated rat cardiomyocytes. Three PLA2 inhibitors, 7, 7-dimethyl-(5Z,8Z)-eicosadienoic acid (DEDA), 3-(4-octadecylbenzoyl)acrylic acid (OBAA), and manoalide, attenuated the LPC-induced accumulation of unsaturated NEFA to a similar degree. Nevertheless, whereas both DEDA and OBAA attenuated the LPC-induced increase in [Ca2+]i, change in cell shape, and release of CK, manoalide attenuated none of them. Reference: Am J Physiol. 1998 Nov;275(5):H1782-7. https://pubmed.ncbi.nlm.nih.gov/9815086/
In vivo activity: The present study examined whether LPC activates phospholipase A2 (PLA2) and whether the activation of PLA2 is responsible for the LPC-induced cell damage in isolated rat cardiomyocytes. Three PLA2 inhibitors, 7, 7-dimethyl-(5Z,8Z)-eicosadienoic acid (DEDA), 3-(4-octadecylbenzoyl)acrylic acid (OBAA), and manoalide, attenuated the LPC-induced accumulation of unsaturated NEFA to a similar degree. Nevertheless, whereas both DEDA and OBAA attenuated the LPC-induced increase in [Ca2+]i, change in cell shape, and release of CK, manoalide attenuated none of them. Reference: Am J Physiol. 1998 Nov;275(5):H1782-7. https://pubmed.ncbi.nlm.nih.gov/9815086/

Preparing Stock Solutions

The following data is based on the product molecular weight 428.66 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
Formulation protocol: 1. Chen M, Xiao CY, Hashizume H, Abiko Y. Phospholipase A2 is not responsible for lysophosphatidylcholine-induced damage in cardiomyocytes. Am J Physiol. 1998 Nov;275(5):H1782-7. doi: 10.1152/ajpheart.1998.275.5.H1782. PMID: 9815086. 2. Köhler T, Heinisch M, Kirchner M, Peinhardt G, Hirschelmann R, Nuhn P. Phospholipase A2 inhibition by alkylbenzoylacrylic acids. Biochem Pharmacol. 1992 Aug 18;44(4):805-13. doi: 10.1016/0006-2952(92)90419-j. PMID: 1324685. 3. Aydinoglu F, Ogulener N. The role of arachidonic acid/cyclooxygenase cascade, phosphodiesterase IV and Rho-kinase in H2S-induced relaxation in the mouse corpus cavernosum. Pharmacol Rep. 2017 Aug;69(4):610-615. doi: 10.1016/j.pharep.2017.02.018. Epub 2017 Feb 24. PMID: 28501682.
In vitro protocol: 1. Chen M, Xiao CY, Hashizume H, Abiko Y. Phospholipase A2 is not responsible for lysophosphatidylcholine-induced damage in cardiomyocytes. Am J Physiol. 1998 Nov;275(5):H1782-7. doi: 10.1152/ajpheart.1998.275.5.H1782. PMID: 9815086. 2. Köhler T, Heinisch M, Kirchner M, Peinhardt G, Hirschelmann R, Nuhn P. Phospholipase A2 inhibition by alkylbenzoylacrylic acids. Biochem Pharmacol. 1992 Aug 18;44(4):805-13. doi: 10.1016/0006-2952(92)90419-j. PMID: 1324685.
In vivo protocol: 1. Aydinoglu F, Ogulener N. The role of arachidonic acid/cyclooxygenase cascade, phosphodiesterase IV and Rho-kinase in H2S-induced relaxation in the mouse corpus cavernosum. Pharmacol Rep. 2017 Aug;69(4):610-615. doi: 10.1016/j.pharep.2017.02.018. Epub 2017 Feb 24. PMID: 28501682. 2. Köhler T, Heinisch M, Kirchner M, Peinhardt G, Hirschelmann R, Nuhn P. Phospholipase A2 inhibition by alkylbenzoylacrylic acids. Biochem Pharmacol. 1992 Aug 18;44(4):805-13. doi: 10.1016/0006-2952(92)90419-j. PMID: 1324685.

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1. Kohler et al (1991) Phospholipase-A2 inhibition by alkylbenzoyl acrylic acids. Agents Actions 32 70 PMID: 2058477