545-46-0

Basic information

• Product Name: UVAOL
• Synonyms: URS-12-ENE-3,28-DIOL;UVAOL;12-URSEN-3B,28-DIOL;12-URSEN-3BETA, 28 DIOL;3B,28-DIHYDROXY-URSA-12-EN;3BETA,28-DIHYDROXY-URSA-12-EN;urs-12-ene-3beta,28-diol;(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-ol
• CAS NO: 545-46-0
• Molecular Formula: C30H50O2
• Molecular Weight: 442.72
• EINECS: 208-888-3
• Product Categories: Tri-Terpenoids
• Mol File: 545-46-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 223-225 °C(lit.)
• Boiling Point: 523.7 °C at 760 mmHg
• Flash Point: 211.6 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 3.73E-13mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 15.09±0.10(Predicted)
• CAS DataBase Reference: UVAOL(CAS DataBase Reference)
• NIST Chemistry Reference: UVAOL(545-46-0)
• EPA Substance Registry System: UVAOL(545-46-0)

Safety Data

• Statements: 22
• Safety Statements: 22-45
• WGK Germany: 3
• Hazardous Substances Data: 545-46-0(Hazardous Substances Data)

Usage

Description

UVAOL, also known as Uvaol, is a natural product derived from the Rhododendron ferrugineum plant. It is a bioactive compound with various pharmacological properties, making it a potential candidate for various applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Applications:
UVAOL is used as an anti-inflammatory agent for attenuating pleuritis and eosinophillic inflammation in mice induced by ovalbumin. Its anti-inflammatory properties make it a promising candidate for the development of new drugs to treat inflammatory conditions.
Used in Chemical Synthesis:
UVAOL serves as an essential reagent in the synthesis of aminopropoxytriterpenoids, which are compounds with demonstrated anticancer activity. Its role in the synthesis process highlights its importance in the development of novel anticancer drugs.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, UVAOL's role in the synthesis of anticancer compounds suggests that it may also be used as a precursor for developing new cancer treatments. Further research and development in this area could potentially lead to the discovery of more effective cancer therapies.

InChI:InChI=1/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3/t19-,20+,22?,23?,24+,25+,27+,28-,29-,30-/m1/s1

Upstream product

• 77-52-1 ursolic acid 
• 74984-68-2 3β-hydroxy-urs-12-en-28-oic acid methyl ester 
• 915-79-7 (3β)-3-acetoxy-urs-12-en-28-carboxylic acid 
• 990-89-6 methyl 3-acetylursolate 
• 86360-96-5 C₃₀H₄₉BrO₂ 
• 25089-86-5 3β-acetoxy-28-hydroxy-urs-12-ene 
• 915-32-2 methyl (3β)-3-hydroxyurs-12-en-28-oate 
• 86996-88-5 3β-acetoxyurs-12-en-28-al 

Downstream Products

• 19132-81-1 ursolic aldehyde 

Relevant articles and documents

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Biocatalytic allylic hydroxylation of unsaturated triterpenes and steroids by Bacillus megaterium CGMCC 1.1741

In this study, we described the microbial catalyzed allylic oxidation by Bacillus megaterium CGMCC 1.1741 of three Δ12-pentacyclic triterpenes, erythrodiol (1), uvaol (2), hederagenin (3) and of four steroids including Δ5-steroids, diosgenin (4), pennogenin (5), 25(R,S)-ruscogenin (6) and Δ4-steroid, diosgenone (7). As a result, fourteen metabolites were generated with allyl hydroxyl moiety. Ten (1a-c, 2a, 2c, 3a, 5a-b, and 6a-b) of them were new natural products and their structures were determined on the basis of 1D/2D NMR and HR-MS data. Biocatalytic allylic oxidation by B. megaterium CGMCC 1.1741 is thus a potential non-toxic and efficient alternative method toward metal-mediated oxidation procedures in the synthesis of natural products and medicines.

Ursolic acid derivatives as potential antidiabetic agents: In vitro, in vivo, and in silico studies

(Table presented.). Protein tyrosine phosphatase 1B (PTP-1B) has attracted interest as a novel target for the treatment of type 2 diabetes, this because its role in the insulin-signaling pathway as a negative regulator. Thus, the aim of current work was to obtain seven ursolic acid derivatives as potential antidiabetic agents with PTP-1B inhibition as main mechanism of action. Furthermore, derivatives 1–7 were submitted in vitro to enzymatic PTP-1B inhibition being 3, 5, and 7 the most active compounds (IC50?=?5.6, 4.7, and 4.6?μM, respectively). In addition, results were corroborated with in silico docking studies with PTP-1B orthosteric site A and extended binding site B, showed that 3 had polar and Van der Waals interactions in both sites with Lys120, Tyr46, Ser216, Ala217, Ile219, Asp181, Phe182, Gln262, Val49, Met258, and Gly259, showing a docking score value of ?7.48?Kcal/mol, being more specific for site A. Moreover, compound 7 showed polar interaction with Gln262 and Van der Waals interactions with Ala217, Phe182, Ile219, Arg45, Tyr46, Arg47, Asp48, and Val49 with a predictive docking score of ?6.43?kcal/mol, suggesting that the potential binding site could be localized in the site B adjacent to the catalytic site A. Finally, derivatives 2 and 7 (50?mg/kg) were selected to establish their in vivo antidiabetic effect using a noninsulin-dependent diabetes mice model, showing significant blood glucose lowering compared with control group (p?.05).