1724-17-0

Basic information

• Product Name: Methyl oleanolate
• Synonyms: METHYLOLEANOLATE;OLEANOLIC ACID METHYL ESTER;methyl (3beta)-3-hydroxyolean-12-en-28-oate;(3β)-3-Hydroxy-olean-12-en-28-oic acid methyl ester;OLEANOLIC ACID METHYL ESTER hplc;OLEANOLIC ACID METHYLESTER WITH HPLC;(3beta)-3-Hydroxy-olean-12-en-28-oic acid methyl ester;3β-Hydroxyolean-12-en-28-oic acid methyl ester
• CAS NO: 1724-17-0
• Molecular Formula: C₃₁H₅₀O₃
• Molecular Weight: 470.73
• EINECS: 217-029-1
• Product Categories: Pentacyclic triterpenes;Tri-Terpenoids
• Mol File: 1724-17-0.mol
• Article Data: 96

Chemical Properties

• Melting Point: 200-205°C
• Boiling Point: 526.1oCat760mmHg
• Flash Point: 190.7oC
• Appearance: /
• Density: 1.07g/cm³
• PKA: 15.15±0.70(Predicted)
• CAS DataBase Reference: Methyl oleanolate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl oleanolate(1724-17-0)
• EPA Substance Registry System: Methyl oleanolate(1724-17-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-36/37/39
• Hazardous Substances Data: 1724-17-0(Hazardous Substances Data)

Usage

General Description

Methyl oleanolate is a chemical compound derived from oleanolic acid, a naturally occurring pentacyclic triterpenoid found in various plant species. It is commonly used in the pharmaceutical and cosmetic industries for its anti-inflammatory, anti-oxidant, and anti-tumor properties. Methyl oleanolate has been studied for its potential as a drug candidate for the treatment of various diseases, including cancer, diabetes, and cardiovascular disorders. Its ability to inhibit the growth of cancer cells and reduce inflammation makes it a promising compound for future therapeutic applications. Additionally, it has also shown potential in skin care products for its anti-aging and skin rejuvenating properties. Overall, methyl oleanolate is a versatile compound with a range of potential medicinal and cosmetic applications.

Upstream product

• 98043-52-8 C₄₂H₆₈O₁₁ 
• 508-02-1 Oleanolic acid 
• 74-88-4 methyl iodide 
• 85031-73-8 (3β,12α) 3,12-diacetoxy-olean-28-oic acid 28,13-lactone 
• 19897-43-9 (3β,12α) 3,12-dihydroxy-18β-olean-28-oic acid 28,13-lactone 
• 62498-83-3 (3β,12α) 3-acetyl-12-hydroxy-18β-olean-28-oic acid 28,13-lactone 
• 80135-32-6 saponin-C methylester 
• 29014-88-8 saponin-D methylester 
• 75804-23-8 C₅₄H₉₀O₁₅ 
• 75804-23-8 C₅₄H₉₀O₁₅ 
• 80145-52-4 saponin-D 
• 80135-33-7 saponin-C 
• 186581-53-3 diazomethane 
• 508-02-1 oleanolic acid 

Downstream Products

• 25493-69-0 (4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 
• 508-02-1 Oleanolic acid 
• 1724-18-1 methyl 3(4)->5-abeo-3,12-oleandien-28-oate 
• 211516-63-1 (3aR,5aR,5bS,7aS,11aS,13aR,13bR)-5a,5b,10,10,13b-Pentamethyl-3-oxo-1,2,3,3a,4,5,5a,5b,6,7,8,9,10,11,11a,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-7a-carboxylic acid methyl ester 
• 1079340-38-7 3-(4-carboxy-benzyloxy)-oleanolic methyl ester 
• 1079340-30-9 C₃₉H₅₆O₅ 
• 1079340-26-3 C₃₈H₅₆O₃ 
• 1079340-34-3 C₃₉H₅₆O₅ 

Relevant articles and documents

Water-induced gel formation of an oleanlic acid-adenine conjugate and the effects of uracil derivative on the gel stability

The conjugate of oleanlic acid with adenine was synthesized and it could be gelled in mixed solvents of THF and water, but no gel was formed in the single organic solvent. The self-aggregation behaviour and physical properties of the organogel were characterized by 1H NMR, FT-IR, and scanning electron microscopy. The morphology and the stability of the gel were remarkably affected by the uracil derivative through destroying hydrogen-bonding.

Studies on differentiation-inducing activities of triterpenes

Differentiation-inducing activity of over 180 extracts of crude drugs and plants was tested using mouse myeloid leukemia cell line (M1). The methanol extracts of clove (Syzygium aromaticum MERRILL et PERRY, Myrtaceae) showed remarkable induction of differentiation of M1 cells into macrophage-like cells. From the extract, oleanolic acid (1) and crategolic acid (2) were isolated as the active components. We also tested other triterpenes, such as oleananes, ursanes and dammaranes, to investigate the structure-activity relationship. Some triterpene aglycones showed differentiation inducing activity, but triterpene glycosides showed little activity. Furthermore, the differentiation-inducing activity of these triterpene compounds was tested against human acute promyelocytic leukemia cell line (HL-60).

TWO SAPONINS FROM ZEXMENIA BUPHTHALMIFLORA

Oleanolic acid 3-O-(3'-O-α-L-rhamnopyranosyl)-β-D-glucuronopyranoside and its 28-O-β-D-glucopyranosyl ester have been isolated from aerial parts of Zexmenia buphthalmiflora.The chemotaxonomical significance of the transfer of Wedelia buphthalmiflora to Zexmenia buphthalmiflora is discussed. Key Word Index - Zexmenia buphthalmiflora; Wedelia buphthalmiflora; Heliantheae; Compositae; structure elucidation; saponins; oleanolic acid 3-O-(3'-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside; oleanolic acid 3-O-(3'-O-α-L-rhamnopyranosyl)-β-D-glucuronopyranoside-28-O-β-D-glucopyranoside.

Partial synthesis of krukovines A and B, triterpene ketones isolated from the Brazilian medicinal plant Maytenus krukovii

Krukovines A (1) and B (2), triterpene ketones isolated from the Brazilian medicinal plant 'chuchuhuasi' (Maytenus krukovii), were synthesized in eight steps from the commercially available oleanolic acid and ursolic acid, respectively.

Synthesis and anion recognition of a novel oleanolic acid-based cyclic dimer

A novel cyclic dimer based on oleanolic acid was synthesized using click chemistry and it showed remarkable selectivity and affinity to bind fluoride ion through C-H...F hydrogen bond interactions which involved the delocalization of proton in methylene.

Radical-Induced Deoxygenation of Primary Alcohols

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On the saponins from the leaves of Fatsia japonica Decne. et Planch.

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Type and position of linkage govern the cytotoxicity of oleanolic acid rhodamine B hybrids

Oleanolic acid/rhodamine B hybrids exhibit different cytotoxicity depending on the way these two structural elements are linked. While a hybrid holding a piperazinyl spacer at C-28 proved to be cytotoxic in the nano-molar concentration range, hybrids with a direct linkage of the Rho B residue to C-3 of the triterpenoid skeleton are cytotoxic only in the low micro-molar concentration range without any selectivity. This once again underlines the importance of selecting the right spacer and the most appropriate position on the skeleton of the triterpene to achieve the most cytotoxic hybrids possible.

Application of methyl isocycloenone oleanolate to preparation of medicine for preventing and treating viral hepatitis B

The invention relates to an application of methyl isocycloenone oleanolate to preparation of a medicine for preventing and treating viral hepatitis B, and particularly provides an application of 3 beta-hydroxyl-12-carbonyl oleanane-13 (18)-alkene-28-carboxylic acid methyl ester to preparation of a medicine for resisting hepatitis B virus infection diseases. A compound has remarkable effect of inhibiting the activity of HBsAg and HBeAg secreted by HepG2.2. 15 cells, the intensity of inhibiting HBsAg and HBeAg secretion at the concentration of 100 micrograms/milliliter on the eighth day exceedsthat of positive control medicines namely alpha-interferon and lamivudine, and the inhibition rate of the compound on HBV-DNA replication is higher than 97% under the concentration. The result shows that the methyl isocycloenone oleanolate can be expected to be used for preparing non-nucleoside medicines for treating hepatitis B virus infection diseases; and specifically, the compound has the functions of being used for preparing an HBV-DNA inhibitor, an HBsAg inhibitor and an HBeAg inhibitor, and the preparation method is simple in step, low in cost, wide in raw material source and easy for industrial production.