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MedKoo Cat#: 574585 | Name: OBAA
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Description:

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

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

Chemical Structure

OBAA
OBAA
CAS#221632-26-4

Theoretical Analysis

MedKoo Cat#: 574585

Name: OBAA

CAS#: 221632-26-4

Chemical Formula: C28H44O3

Exact Mass: 428.3290

Molecular Weight: 428.66

Elemental Analysis: C, 78.46; H, 10.35; O, 11.20

Price and Availability

Size Price Availability Quantity
50mg USD 750.00 2 Weeks
100mg USD 1,250.00 2 Weeks
200mg USD 2,050.00 2 Weeks
500mg USD 3,250.00 2 Weeks
1g USD 4,650.00 2 Weeks
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Related CAS #
No Data
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
Product Data
Instruction
View handling instruction
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.
1. Kohler et al (1991) Phospholipase-A2 inhibition by alkylbenzoyl acrylic acids. Agents Actions 32 70 PMID: 2058477

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