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

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

Uses

Used in Pharmaceutical Industry:
Methyl oleanolate is used 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.
Used in Cosmetic Industry:
Methyl oleanolate is used as an ingredient in skin care products for its anti-aging and skin rejuvenating properties. Its anti-oxidant and anti-inflammatory properties contribute to the overall health and appearance of the skin.

Upstream product

• 508-02-1 oleanolic acid 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 1721-58-0 methyl 3-oxooleanolate 
• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 508-02-1 Oleanolic acid 
• 77-78-1 dimethyl sulfate 
• 117804-22-5 cynarasaponin H methyl ester 
• 95851-48-2 C₄₂H₆₈O₁₂ 
• 79542-22-6 (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-methylsulfanylthiocarboxyoxymethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester 
• 89837-91-2 C₄₈H₇₈O₁₃ 
• 101021-04-9 C₅₆H₉₄O₁₆ 
• 90138-33-3 C₅₇H₉₄O₁₈ 

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.

Protein tyrosine phosphatase 1B inhibitory activity of triterpenes isolated from Astilbe koreana

Bioassay-guided fractionation of a MeOH extract of the rhizomes of Astilbe koreana (Saxifragaceae), using an in vitro protein tyrosine phosphatase 1B (PTP1B) inhibitory assay, resulted in the isolation of a new triterpene, 3α,24-dihydroxyolean-12-en-27-oic acid (4), along with four triterpenes, 3-oxoolean-12-en-27-oic acid (1), 3β-hydroxyolean-12-en-27-oic acid (β-peltoboykinolic acid; 2), 3β-hydroxyurs-12-en-27-oic acid (3), and 3β,6β-dihydroxyolean-12-en-27-oic acid (astilbic acid; 5). Compounds 1-5 inhibited PTP1B with IC50 values of 6.8 ± 0.5, 5.2 ± 0.5, 4.9 ± 0.4, 11.7 ± 0.9, and 12.8 ± 1.1 μM, respectively. Our results indicate that 3-hydroxyl group and a carboxyl group in this type of triterpenes may be required for the activity, while addition of one more hydroxyl group at C-6 or C-24 may be responsible for a loss of activity. Thus, compounds 2 and 3 which possess only one hydroxyl group at C-3 and a carboxyl group at C-27 could be potential PTP1B inhibitors.

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).

Efficient and scalable synthesis of bardoxolone methyl (CDDO-methyl ester)

Bardoxolone methyl (2-cyano-3,12-dioxooleane-1,9(11)-dien-28-oic acid methyl ester; CDDO-Me) (1), a synthetic oleanane triterpenoid with highly potent anti-inflammatory activity (levels below 1 nM), has completed a successful phase I clinical trial for the treatment of cancer and a successful phase II trial for the treatment of chronic kidney disease in type 2 diabetes patients. Our synthesis of bardoxolone methyl (1) proceeds in ～50% overall yield in five steps from oleanolic acid (2), requires only one to two chromatographic purifications, and can provide gram quantities of 1.

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.

NEO-CLERODANE DITERPENOIDS FROM BACCHARIS MACRAEI

Key Word Index - Baccharis macraei; Compositae; diterpenes; neo-clerodanes. From the aerial parts of Baccharis macraei two new clerodane diterpenes, bacchasmacranone and 2β-hydroxybacchasmacranone, were isolated besides the known hardwickiic and hautriwaic acids.The structures of the new compounds were elucidated by spectroscopic methods.

Biotransformation of oleanolic and maslinic methyl esters by Rhizomucor miehei CECT 2749

The pentacyclic triterpenoids methyl oleanolate, methyl maslinate, methyl 3β-hydroxyolean-9(11),12-dien-28-oate, and methyl 2α,3β-dihydroxy-12β,13β-epoxyolean-28-oate were biotransformed by Rhizomucor miehei CECT 2749. Microbial transformation of methyl oleanolate produced only a 7β,30-dihydroxylated metabolite with a conjugated 9(11),12-diene system in the C ring. Biotransformation of the substrate with this 9(11),12-diene system gave the same 7β,30-dihydroxylated compound together with a 7β,15α,30-trihydroxyl derivative. The action of this fungus (R. miehei) on methyl maslinate was more varied, isolating metabolites with a 30-hydroxyl group, a 9(11),12-diene system, an 11-oxo group, or an 12-oxo group. Microbial transformation of the substrate with a 12β,13β-epoxy function resulted in the isolation of two metabolites with 12-oxo and 28,13β-olide groups, hydroxylated or not at C-7β, together with a 30-hydroxy-12-oxo derivative. The structures of these derivatives were deduced by extensive and rigorous spectroscopic studies.

Pentacylic triterpenes from Lavandula coronopifolia: structure related inhibitory activity on α-glucosidase

Ten pentacyclic triterpenes (1-10) were isolated from Lavandula coronopifolia. We evaluated their α-glucosidase inhibitory activity, and found that the aglycones, 1, 2, 3, 4, 7 and 10 showed superior IC50 values to the positive control. In order to explain the structural requirements for α-glucosidase inhibitory activity, eleven derivatives were prepared, including one new compound, 2-formyl-(A)1–19α-hydroxy-1-norursane-2, 12-dien-28-oic acid 10c. The results demonstrated that a free hydroxyl at ring-A and a free carboxylic group at position 28 are key structural features for the α-glucosidase inhibitory activity, also that an ursane skeleton is optimum for the activity. Additionally, enzyme kinetic analysis of pomolic acid 2, the most potent compound, revealed that it inhibited α-glucosidase in a mixed-type manner. The molecular docking simulation validated this type of inhibition and highlighted the role of the C-3 hydroxyl and C-28 carboxylic groups in interaction with the enzyme in silico.