85999-40-2

Basic information

• Product Name: 23-HYDROXYBETULINIC ACID
• Synonyms: ANEMOSAPOGININ;23-HYDROXYBETULINIC ACID;3β,23-Dihydroxylup-20(29)-en-28-oic acid;3beta,23-Dihydroxylup-20(29)-en-28-oic acid;Anemosapogenin,23-Hydroxybetulinic acid
• CAS NO: 85999-40-2
• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.7
• Product Categories: Miscellaneous Natural Products
• Mol File: 85999-40-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 585.787 °C at 760 mmHg
• Flash Point: 322.11 °C
• Appearance: /
• Density: 1.106
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly, Heated), Pyridine (Slightly)
• PKA: 4.60±0.70(Predicted)
• CAS DataBase Reference: 23-HYDROXYBETULINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 23-HYDROXYBETULINIC ACID(85999-40-2)
• EPA Substance Registry System: 23-HYDROXYBETULINIC ACID(85999-40-2)

Safety Data

• Hazardous Substances Data: 85999-40-2(Hazardous Substances Data)

Usage

Description

23-hydroxy Betulinic acid is a triterpenoid that has been found in P. chinensis and has anticancer activity. It inhibits proliferation of K562, B16, and HeLa cells (IC50s = 39.9, 78.5, and 80 μM, respectively), as well as human umbilical vein endothelial cells (HUVECs; IC50 = 94.8 μM). It halts the cell cycle at the S phase and induces apoptosis in K562 cells in a concentration-dependent manner with a loss of the mitochondrial membrane potential and an increase in Bax and cytochrome C protein levels.

Uses

23-Hydroxybetulinic Acid is a potential cytoxic agent in the treatment of cancer. Apoptotic effect. Antiproliferative.

InChI:InChI=1/C30H48O4/c1-18(2)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h19-24,31-32H,1,7-17H2,2-6H3,(H,33,34)/t19-,20-,21+,22+,23-,24+,26-,27-,28+,29+,30-/m0/s1

Upstream product

• 1215746-83-0 benzyl 3,23-dihydroxy-lup-20⁽²⁹⁾-en-28-oate 
• 203576-71-0 benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-oxo-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate 
• 192211-42-0 benzyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate 
• 472-15-1 Betulinic acid 
• 1256959-25-7 benzyl 3-oxo-23-hydroxy-lup-20⁽²⁹⁾-en-28-oate 
• 1256959-24-6 benzyl 3-hydroxyimino-23-hydroxy-lup-20⁽²⁹⁾-en-28-oate 
• 1256959-23-5 benzyl 3-acetoxyimino-23-acetoxy-lup-20⁽²⁹⁾-en-28-oate 
• 1256959-22-4 benzyl 3-hydroxyimino-lup-20⁽²⁹⁾-en-28-oate 
• 136684-40-7 benzyl 3-oxo-23-hydroxy-lup-20⁽²⁹⁾-en-28-oic acid 
• 129724-84-1 DA₀₀₁ 
• 129741-57-7 chinensioside A 

Downstream Products

• 85999-41-3 3,23-diacetoxylup-20⁽²⁹⁾-en-28-oic acid 
• 1082746-38-0 3-hydroxy-23-acetoxylup-20⁽²⁹⁾-en-28-oic acid 
• 1082746-37-9 3-acetoxy-23-hydroxy-20⁽²⁹⁾-lupen-28-oic acid 
• 85999-42-4 3,23-dihydroxy-20⁽²⁹⁾-lupen-28-oic acid methyl ester 
• 1082746-64-2 3,23-di-tert-butyldimethylsililoxy-20⁽²⁹⁾-lupen-28-oic acid 
• 1082746-35-7 3,23-dihydroxy-20⁽²⁹⁾-lupen-28-oic acid ethyl ester 
• 1082746-58-4 3,23-dihydroxy-20⁽²⁹⁾-lupen-28-oic acid 2,2-dimethyl-1,3-dioxolane-4-yl methyl ester 
• 1082746-36-8 3,23-dihydroxy-20⁽²⁹⁾-lupan-28-oic acid 
• 1082746-39-1 3,23-dihydroxy-20⁽²⁹⁾-epoxy-lupan-28-oic acid 
• 1544635-04-2 2-[[N-[3β,23-dihydroxylup-20(29)-en-28-oyl]-3-aminopropyl]carbamoyl]benzoic acid 
• 1544635-02-0 N-[3-N-[(3β,23-dihydroxylup-20(29)-en-28-oyl)]propyl]propanamide 
• 1544634-96-9 [[N-[3β,23-dihydroxylup-20(29)-en-28-oyl]-7-aminoheptyl]carbamoyl]propanoic acid 
• 1544634-94-7 N-[3β,23-diacetoxylup-20(29)-en-28-oyl]-1,7-diaminoheptane 
• 1204202-56-1 N-[3β,23-diacetoxylup-20(29)-en-28-oyl]-1,6-diaminohexane 

Relevant articles and documents

A New Lupane-Type Triterpenoid Saponin from Lonicera macranthoides

A new lupane-type triterpenoid saponin, named lonimacranthoside A 1, was isolated from the flower buds of Lonicera macranthoides. The structure of lonimacranthoside A1 was elucidated as 3β-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl-23- hydroxy-lup-20(29)-en-28-oic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (1) on the basis of spectral data and chemical evidence. This is the first reported occurrence of a lupane-type saponin in the plant.

Improving Physical Properties via C-H Oxidation: Chemical and Enzymatic Approaches

Physicochemical properties constitute a key factor for the success of a drug candidate. Whereas many strategies to improve the physicochemical properties of small heterocycle-type leads exist, complex hydrocarbon skeletons are more challenging to derivatize because of the absence of functional groups. A variety of C-H oxidation methods have been explored on the betulin skeleton to improve the solubility of this very bioactive, yet poorly water-soluble, natural product. Capitalizing on the innate reactivity of the molecule, as well as the few molecular handles present on the core, allowed oxidations at different positions across the pentacyclic structure. Enzymatic oxidations afforded several orthogonal oxidations to chemical methods. Solubility measurements showed an enhancement for many of the synthesized compounds. A handle on [O]: A variety of C-H oxidation methods were explored on the betulin skeleton to improve the solubility of this bioactive, yet poorly water-soluble, natural product. The innate reactivity of the molecule, as well as the molecular handles present on the core, allowed oxidations at different positions. Solubility enhancement was observed for many of the synthesized compounds.

23-Substituted Derivatives of Lupane-type Pentacyclic Triterpenoids

The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprises pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.