Oleanolic acid acrylate
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MedKoo CAT#: 574047

CAS#: 1975976-24-9

Description: Oleanolic acid acrylate (OAA) is an agonist of the serotonin (5-HT) receptor subtype 5-HT1A and a derivative of oleanolic acid. It is also a selective inhibitor of MAO-A with anti-depressant-like and anxiolytic activities.

Chemical Structure

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Oleanolic acid acrylate
CAS# 1975976-24-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 574047
Name: Oleanolic acid acrylate
CAS#: 1975976-24-9
Chemical Formula: C33H50O4
Exact Mass: 510.37
Molecular Weight: 510.759
Elemental Analysis: C, 77.60; H, 9.87; O, 12.53

Price and Availability

Size Price Availability Quantity
1mg USD 215
5mg USD 450
10mg USD 730
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Synonym: Oleanolic acid acrylate, OAA

IUPAC/Chemical Name: (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acryloyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid

InChi Key: SEOUKQFSVNKQNN-FBXMHRQLSA-N

InChi Code: InChI=1S/C33H50O4/c1-9-26(34)37-25-13-14-30(6)23(29(25,4)5)12-15-32(8)24(30)11-10-21-22-20-28(2,3)16-18-33(22,27(35)36)19-17-31(21,32)7/h9-10,22-25H,1,11-20H2,2-8H3,(H,35,36)/t22-,23-,24+,25-,30-,31+,32+,33-/m0/s1

SMILES Code: CC1(C)CC[C@]2(C(O)=O)CC[C@@]3(C)[C@]4(C)CC[C@@]5([H])C(C)(C)[C@@H](OC(C=C)=O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])C1

Appearance: Solid powder

Purity: >95% (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:
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Biological target: Oleanolic acid acrylate (OAA) is an agonist of the serotonin (5-HT) receptor subtype 5-HT1A and a derivative of oleanolic acid.
In vitro activity: OAA (oleanic acid acetate) reduced OVA-induced airway inflammatory responses such as bronchospasm, increase of immune cell infiltration and serum immunoglobulin E and G1 levels. Especially, OAA decreased the mast cell infiltration, and β-hexosaminidase release as a mast cell activation marker in the bronchoalveolar lavage fluid. OAA inhibited mast cell degranulation in mast cell line (RBL-2H3) and primary cells (rat peritoneal mast cell and mouse bone marrow-derived mast cell). Mechanistically, OAA suppressed intracellular signaling pathways including the phosphorylation of phospholipase Cγ and nuclear factor-κB, resulting from the suppression of intracellular calcium influx and pro-inflammatory cytokine expression. Reference: Allergy Asthma Immunol Res. 2023 Mar;15(2):214-230. https://pubmed.ncbi.nlm.nih.gov/37021507/
In vivo activity: Rats treated with 10% w/v fructose solution were co-administered by OA (oleanolic acid) for 5 weeks, and then sacrificed after fasting for 14 h. OA reversed the fructose-induced increase in hepatic triglyceride (TG) content and downregulated Scd1 mRNA expression. In vivo and in vitro studies using SREBP1c-/- mice and HepG2 cell models showed that OA also inhibited SCD1 gene overexpression and high hepatic TG levels induced by fructose. On the other hand, in SCD1-/- mice, when the fructose diet was supplemented with high levels of oleic acid (OLA) to compensate for the deficiency of SCD1, OA inhibited hepatic SREBP1c and lipogenic gene expression and reduced hepatic OLA (C18:1) production to improve fructose and/or OLA induced liver lipid deposition. Furthermore, OA promoted PPARα and AMPK to enhance fatty acid oxidation in fructose + OLA-fed SCD1-/- mice. Reference: Mol Nutr Food Res. 2023 Mar 27:e2200533. https://pubmed.ncbi.nlm.nih.gov/36972071/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 58.74
DMSO 20.0 39.16
Ethanol 30.0 58.74
Ethanol:PBS (pH 7.2) (1:40) 0.0 0.04

Preparing Stock Solutions

The following data is based on the product molecular weight 510.76 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. Kim YY, Lee S, Kim MJ, Rho MC, Jang YH, Kim SH. Oleanolic Acid Acetate Inhibits Mast Cell Activation in Ovalbumin-Induced Allergic Airway Inflammation. Allergy Asthma Immunol Res. 2023 Mar;15(2):214-230. doi: 10.4168/aair.2023.15.2.214. PMID: 37021507; PMCID: PMC10079514. 2. Luo Y, Wang D, Yuan X, Jin Z, Pi L. Oleanolic acid regulates the proliferation and extracellular matrix of keloid fibroblasts by mediating the TGF-β1/SMAD signaling pathway. J Cosmet Dermatol. 2023 Feb 27. doi: 10.1111/jocd.15673. Epub ahead of print. PMID: 36847714. 3. Zhang B, Zhang W, Luo J, He J, Zheng X, Zhu S, Rong B, Ai Y, Zhang L, He T. Effects of oleanolic acid on hair growth in mouse dorsal skin mediated via regulation of inflammatory cytokines. J Appl Biomed. 2023 Apr;21(1):48-57. doi: 10.32725/jab.2023.003. Epub 2023 Mar 27. PMID: 37016778. 4. Yao L, Wang M, Zhang J, Luo X, Yuan C, Bai R, Wang T, Xi Y, Li C, Ke D, Yamahara J, Li Y, Yi Y, Wang S, Wang J. Oleanolic Acid Inhibits SCD1 Gene Expression to Ameliorate Fructose-Induced Hepatosteatosis through SREBP1c-Dependent and -Independent Mechanisms. Mol Nutr Food Res. 2023 Mar 27:e2200533. doi: 10.1002/mnfr.202200533. Epub ahead of print. PMID: 36972071.
In vitro protocol: 1. Kim YY, Lee S, Kim MJ, Rho MC, Jang YH, Kim SH. Oleanolic Acid Acetate Inhibits Mast Cell Activation in Ovalbumin-Induced Allergic Airway Inflammation. Allergy Asthma Immunol Res. 2023 Mar;15(2):214-230. doi: 10.4168/aair.2023.15.2.214. PMID: 37021507; PMCID: PMC10079514. 2. Luo Y, Wang D, Yuan X, Jin Z, Pi L. Oleanolic acid regulates the proliferation and extracellular matrix of keloid fibroblasts by mediating the TGF-β1/SMAD signaling pathway. J Cosmet Dermatol. 2023 Feb 27. doi: 10.1111/jocd.15673. Epub ahead of print. PMID: 36847714.
In vivo protocol: 1. Zhang B, Zhang W, Luo J, He J, Zheng X, Zhu S, Rong B, Ai Y, Zhang L, He T. Effects of oleanolic acid on hair growth in mouse dorsal skin mediated via regulation of inflammatory cytokines. J Appl Biomed. 2023 Apr;21(1):48-57. doi: 10.32725/jab.2023.003. Epub 2023 Mar 27. PMID: 37016778. 2. Yao L, Wang M, Zhang J, Luo X, Yuan C, Bai R, Wang T, Xi Y, Li C, Ke D, Yamahara J, Li Y, Yi Y, Wang S, Wang J. Oleanolic Acid Inhibits SCD1 Gene Expression to Ameliorate Fructose-Induced Hepatosteatosis through SREBP1c-Dependent and -Independent Mechanisms. Mol Nutr Food Res. 2023 Mar 27:e2200533. doi: 10.1002/mnfr.202200533. Epub ahead of print. PMID: 36972071.

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1. Fajemiroye, J.O., Polepally, P.R., Chaurasiya, N.D., et al. Oleanolic acid acrylate elicits antidepressant-like effect mediated by 5-HT1A receptor. Sci. Rep. 5, 11582 (2015).