39111-07-4

Basic information

• Product Name: NIGRANOIC ACID
• Synonyms: NIGRANOIC ACID;(3S,3aR,4aS,6aR,7R,9aS,9bS)-7-[(1R,4Z)-5-Carboxy-1-methyl-4-hexen-1-yl]decahydro-6a,9a-dimethyl-3-(1-methylethenyl)-1H-cyclopenta[a]cyclopropa[e]naphthalene-3a(4H)-propanoic acid
• CAS NO: 39111-07-4
• Molecular Formula: C30H46O4
• Molecular Weight: 470.68
• Mol File: 39111-07-4.mol

Chemical Properties

• Melting Point: 128-130 °C
• Boiling Point: 603°Cat760mmHg
• Flash Point: 332.5°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 4.29E-16mmHg at 25°C
• Refractive Index: 1.549
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: NIGRANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: NIGRANOIC ACID(39111-07-4)
• EPA Substance Registry System: NIGRANOIC ACID(39111-07-4)

Safety Data

• Hazardous Substances Data: 39111-07-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
NIGRANOIC ACID is used as a pharmaceutical compound for its cytotoxic and anti-HIV activities. Its ability to exhibit these properties makes it a potential candidate for the development of new drugs to combat HIV and other related diseases.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, given its cytotoxic properties, NIGRANOIC ACID could potentially be used as an anticancer agent. Further research would be required to explore its efficacy against various types of cancer and its potential synergistic effects when combined with conventional chemotherapeutic drugs.
Used in Drug Delivery Systems:
Similar to gallotannin, NIGRANOIC ACID could benefit from novel drug delivery systems to enhance its applications and efficacy. The development of organic and metallic nanoparticles as carriers for NIGRANOIC ACID delivery could improve its bioavailability and therapeutic outcomes in targeted treatments.

InChI:InChI=1/C30H46O4/c1-19(2)22-12-15-27(5)17-18-30-23(29(22,27)16-13-24(31)32)11-8-14-28(30,6)25(30)20(3)9-7-10-21(4)26(33)34/h10,20,22-23,25H,1,7-9,11-18H2,2-6H3,(H,31,32)(H,33,34)/b21-10-

Upstream product

• 39111-08-5 dimethyl 3,4-secocycloarta-4⁽²⁸⁾,24-(Z)-diene-3,27-dioate 

Relevant articles and documents

Synthesis of nigranoic acid and manwuweizic acid derivatives as HDAC inhibitors and anti-inflammatory agents

As a successful anti-tumor drug target, the family of histone deacetylases (HDACs) is also a critical player in immune response, making the research of anti-inflammatory HDAC inhibitors an attractive new focus. In this report, triterpenoids nigranoic acid (NA) and manwuweizic acid (MA) were identified as HDAC inhibitors through docking-based virtual screening and enzymatic activity assay. A series of derivatives of NA and MA were synthesized and assessed for their biological effects. As a result, hydroxamic acid derivatives of NA and MA showed moderately increased activity for HDAC1/2/4/6 inhibition (the lowest IC50 against HDAC1 is 1.14 μM), with no activity against HDAC8. In J774A.1 macrophage, compound 1–3, 13 and 17–19 demonstrated inhibitory activity against lactate dehydrogenase (LDH) and IL-1β production, without affecting cell viability. Compound 19 increased the histone acetylation level in J774A.1 cells, as well as inhibited IL-1β maturation and caspase-1 cleavage. These results indicated that compound 19 blocks the activation of NLRP3 inflammasome, probably related to HDAC inhibition. This work provided a natural scaffold for developing low-cytotoxic and anti-inflammatory HDAC inhibitors, as well as a class of tool molecules for studying the relationship between HDACs and NLRP3 activation.