(1S,2R,4aS,6aS,6bR,10S,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

Base Information

• Chemical Name: (1S,2R,4aS,6aS,6bR,10S,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• CAS No.: 77-52-1
• Molecular Formula: C30H48O3
• Molecular Weight: 456.709
• Hs Code.: 29181990
• ChEMBL ID: CHEMBL3039159
• Mol file: 77-52-1.mol

Synonyms:(1S,2R,4aS,6aS,6bR,10S,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid;Spectrum_001581;SpecPlus_000130;Spectrum2_001744;Spectrum3_001702;Spectrum4_001655;Spectrum5_000529;Urs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-;BSPBio_003284;KBioGR_002149;KBioSS_002061;DivK1c_006226;SPECTRUM1800031;SPBio_001848;MEGxp0_000293;SCHEMBL9883367;CHEMBL3039159;ACon1_000209;KBio1_001170;KBio2_002061;KBio2_004629;KBio2_007197;KBio3_002504;WCGUUGGRBIKTOS-POPPTPIPSA-N;CCG-38798;SDCCGMLS-0066868.P001;NCGC00178163-01;NCGC00178163-02;NCGC00178163-03;BRD-A34492468-001-02-7;BRD-A34492468-001-04-3

Chemical Property of (1S,2R,4aS,6aS,6bR,10S,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.01E-14mmHg at 25°C
• Melting Point: 292 °C (dec.)(lit.)
• Refractive Index: 1.4940 (estimate)
• Boiling Point: 556.9 °C at 760 mmHg
• PKA: 4.68±0.70(Predicted)
• Flash Point: 304.7 °C
• PSA: 57.53000
• Density: 1.09 g/cm³
• LogP: 7.08950
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml with warming)
• Water Solubility.: insoluble
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 456.36034539
• Heavy Atom Count: 33
• Complexity: 874

Purity/Quality:

98% ^*data from raw suppliers

Ursolic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1C)C)C(=O)O
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CCC4[C@]3(CCC5[C@@]4(CC[C@@H](C5(C)C)O)C)C)C2[C@H]1C)C)C(=O)O
• Chemical Structure and Origin: Ursolic Acid (UA) is a pentacyclic compound with functional groups at specific carbon positions. Initially identified in the 1920s from apple epicuticular waxes and later isolated from various plant organs.
• Biological Activities: UA exhibits diverse biological activities, including anticancer, anti-inflammatory, antimicrobial, and antidiabetic properties. Anticancer effects are demonstrated against various cancer types, targeting multiple molecular pathways involved in cell proliferation, metastasis, apoptosis, angiogenesis, and autophagy. Other reported effects include modulation of cellular transcription factors, growth factor receptors, and cytokines.
• Anti-inflammatory Effects: UA counteracts both endogenous and exogenous inflammatory stimuli.; Mechanisms involve inhibition of histamine release, suppression of enzyme activities (lipoxygenase, cyclooxygenase, phospholipase), and reduction of nitric oxide and reactive oxygen species production.; Downregulates expression of inflammatory factors and inhibits elastase and complement activities.
• Pharmacological Studies: UA is among the most studied triterpenoids due to its wide range of pharmacological activities.; Poor water solubility limits its efficacy, prompting research into structural modifications to enhance its pharmacokinetic profiles and therapeutic effects.; Studies explore strategies to improve solubility and efficacy through structure-activity relationships and molecular modifications.
• Natural Occurrence and Solubility: Found as a secondary metabolite in various plant parts.; Exhibits low polarity and poor water solubility but high solubility in organic solvents like 2-propanol, ethyl acetate, methanol, and ethanol.
• Therapeutic Potential: UA's wide range of beneficial effects, including anticancer, anti-inflammatory, antibacterial, antiprotozoan, antioxidant, antidiabetic, and antiviral properties, suggest its potential as a therapeutic agent. Ongoing research aims to harness UA's pharmacological activities for the development of novel therapeutic approaches targeting various diseases.

Technology Process of (1S,2R,4aS,6aS,6bR,10S,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

There total 11 articles about (1S,2R,4aS,6aS,6bR,10S,12aR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

tert-butyldiphenylsilyl 3-O-(tert-butyldiphenylsilyloxy)ursolate (1381876-19-2) → ursolic acid (77-52-1)

Guidance literature:

With perchloric acid on silica gel; In acetonitrile; at 50 ℃; for 0.5h; chemoselective reaction;

DOI:10.1016/j.carres.2012.02.021

Reference yield: 70.0%

methyl (3β)-3-hydroxyurs-12-en-28-oate (915-32-2,26532-60-5,32208-45-0,74984-68-2,94482-47-0,121468-30-2) → ursolic acid (77-52-1)

Guidance literature:

With lithium; In ethylenediamine; for 4h; Heating;

Reference yield: 25.0%

→ ursolic acid (77-52-1)

Guidance literature:

upstream raw materials:

methyl (3β)-3-hydroxyurs-12-en-28-oate

phenyl-3β-acetoxy-urs-12-en-28-oate

sodium acetate

tert-butyldiphenylsilyl 3-O-(tert-butyldiphenylsilyloxy)ursolate

Downstream raw materials:

methyl 3-acetylursolate

methyl ursonate

3-hydroxyimino-urs-12-en-28-oic acid methyl ester

3-hydroxyimino-urs-12-en-28-oic acid

Refernces

• 1、 Samy, Mamdouh N.,Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki,Kamel, Mohamed S.. "One new flavonoid xyloside and one new natural triterpene rhamnoside from the leaves of Syzygium grande". . p. 86 - 90. Retrieved 2014/12/10.
• 2、 Yan, Shiqiang,Ding, Ning,Zhang, Wei,Wang, Peng,Li, Yingxia,Li, Ming. "An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers". experimental part. p. 6 - 20. Retrieved 2012/07/13.