3Beta-acetoxybetulinic acid

• CAS: 10376-50-8
• Catalog Number: ACM10376508
• Category: Main Products
• Molecular Weight: 498.74
• Molecular Formula: C₃₂H₅₀O₄
• Synonyms: 3-O-Acetyl-betulinic acid;Acetyl betulinic acid
• IUPAC Name: 9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7...
• Boiling Point: 561.1ºC at 760 mmHg
• Flash Point: 169.1ºC
• Density: 1.09 g/cm³
• Appearance: White to off-white solid
• Exact Mass: 498.37100

Case Study

Antioxidant and Anti-Inflammatory Activities of 3β-Acetoxybetulinic Acid

Osunsanmi F O, et al. Tropical Journal of Pharmaceutical Research, 2019, 18(2), 303-309.

Betulinic acid (BA) is a member of the pentacyclic triterpenoids and has anti-angiogenesis, anti-platelet aggregation, anti-sickling and anti-ulcer effects. The study evaluated the antioxidant, anti-inflammatory and anti-acetylcholinesterase activities of BA and its derivative (3β-acetoxybetulinic acid, BAA). The results showed that BA and BAA have anti-acetylcholinesterase (ACHE), anti-inflammatory, antioxidant and anti-cyclooxygenase (COX) activities. Therefore, 3β-acetoxybetulinic acid could serve as a scaffold for the synthesis of effective drugs for neurodegenerative diseases.
Preparation of 3β-acetoxybetulinic acid
· Betulinic acid (3 g) were dissolved in a round bottom flask (50 mL) containing acetic anhydride (12 mL) and pyridine (10 mL). This was refluxed (40 ◦C; 10 h) in a fume cupboard.
· The reaction was terminated with distilled water (25 mL). The solution was then stirred (45 min) and filtered with whatman filter paper. Excess pyridine was washed off from the residue using hydrochloric acid (12 %).
· The dried residue was purified by column chromatography. Fifty fraction (20 mL) were collected, and identical fractions were combined. This was then concentrated in vacuo at 40 °C. The compound was recrystallized using methanol, yielding yellowish powder.

Antiplatelet Aggregation and Cytotoxic Activities of Betulinic Acid and 3Β-Acetoxybetulinic Acid

Osunsanmi F O, et al. Journal of Medicinal Plants Research, 2015, 9(22), 647-654.

Betulinic acid (BA) is a naturally occurring pentacyclic triterpene with multiple biological activities. 3β-acetoxybetulinic acid (BAA) is an acetyl derivative of BA. The antiplatelet aggregation and cytotoxic activities of BA isolated from Melaleuca leucophylla leaf extract and its acetyl derivative BAA were studied. The results show that both betulinic acid and 3β-acetoxybetulinic acid have anti-platelet aggregation activity. In addition to efficacy, the weak cytotoxic effects exhibited by these compounds suggest their potential use as templates for the synthesis of safe pharmacologically active antiplatelet drugs.
Synthesis of 3β-acetoxybetulinic acid
· BA (2 g) isolated from the M. bracetata was dissolved in a mixture of pyridine (10 ml) and acetic anhydride (12 ml) in a round bottom flask. The mixture was refluxed for 6 h at room temperature (25°C).
· The reaction was then terminated with addition of distilled water (25 ml). The mixture was further stirred with magnetic rod for 45 min. The filtrate was washed with HCl (12%) to remove excess pyridine, concentrated by suction and air-dried.
· The synthesized compound was further subjected to silica gel (60 × 120 mesh) column chromatography (20 × 5.5 mm) for purification. BAA was recrystallized with methanol to obtain a white powder.

Custom Q&A

What is the molecular formula of 3Beta-acetoxybetulinic acid?

The molecular formula of 3Beta-acetoxybetulinic acid is C32H50O4.

What are some synonyms of 3Beta-acetoxybetulinic acid?

Some synonyms of 3Beta-acetoxybetulinic acid are Betulinic acid acetate, Acetylbetulinic acid, and 3-O-Acetylbetulinic acid.

What is the molecular weight of 3Beta-acetoxybetulinic acid?

The molecular weight of 3Beta-acetoxybetulinic acid is 498.7 g/mol.

When was 3Beta-acetoxybetulinic acid created?

3Beta-acetoxybetulinic acid was created on March 26, 2005.

When was 3Beta-acetoxybetulinic acid last modified?

3Beta-acetoxybetulinic acid was last modified on December 2, 2023.

Where can 3Beta-acetoxybetulinic acid be found?

3Beta-acetoxybetulinic acid can be found in Eucalyptus globulus, Monascus purpureus, and other organisms.

What is the IUPAC name of 3Beta-acetoxybetulinic acid?

The IUPAC name of 3Beta-acetoxybetulinic acid is 9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid.

What is the InChI of 3Beta-acetoxybetulinic acid?

The InChI of 3Beta-acetoxybetulinic acid is InChI=1S/C32H50O4/c1-19(2)21-11-16-32(27(34)35)18-17-30(7)22(26(21)32)9-10-24-29(6)14-13-25(36-20(3)33)28(4,5)23(29)12-15-31(24,30)8/h21-26H,1,9-18H2,2-8H3,(H,34,35).

How many hydrogen bond acceptor counts does 3Beta-acetoxybetulinic acid have?

3Beta-acetoxybetulinic acid has 4 hydrogen bond acceptor counts.