51415-07-7

Basic information

• Product Name: momilactone A
• Synonyms: momilactone A;(3aR)-8α-Vinyl-2,3a,8,9,10,10aα,10b,10cβ-octahydro-3aβ,8,10bα-trimethyl-1H-phenanthro[10,1-bc]furan-3,4(5aβH,7H)-dione;8α-Vinyl-2,3a,8,9,10,10aα,10b,10cβ-octahydro-3aβ,8,10bα-trimethyl-1H-phenanthro[10,1-bc]furan-3,4(5aβH,7H)-dione
• CAS NO: 51415-07-7
• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.41864
• Mol File: 51415-07-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 235-236 °C
• Boiling Point: 460.1°C at 760 mmHg
• Flash Point: 201.8°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 1.2E-08mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: momilactone A(CAS DataBase Reference)
• NIST Chemistry Reference: momilactone A(51415-07-7)
• EPA Substance Registry System: momilactone A(51415-07-7)

Safety Data

• Hazardous Substances Data: 51415-07-7(Hazardous Substances Data)

Usage

Description

Momilactone A, a secondary plant metabolite, is a diterpenoid phytoalexin with potent antimicrobial properties. It is produced by rice (Oryza sativa) and moss (Hypnum plumaeforme) in response to infection and exposure to ultraviolet (UV) light. This unique compound contributes to the plants' defense mechanisms against various pathogens.

Uses

Used in Agriculture:
Momilactone A is used as a natural antimicrobial agent for protecting crops from various diseases caused by fungi, bacteria, and other pathogens. Its production in response to plant infection and UV light exposure makes it an essential component in the plants' defense system, helping to reduce crop losses and improve overall yield.
Used in Pharmaceutical Industry:
Momilactone A is used as a potential therapeutic agent due to its antimicrobial properties. It can be explored for the development of new drugs targeting resistant strains of bacteria and fungi, contributing to the fight against antibiotic and antifungal resistance.
Used in Cosmetics:
In the cosmetics industry, momilactone A can be used as a natural preservative due to its antimicrobial activity. This application can help extend the shelf life of cosmetic products and maintain their safety and efficacy.
Used in Food Industry:
Momilactone A can be employed as a natural preservative in the food industry to prevent spoilage and extend the shelf life of perishable products. Its antimicrobial properties can help control the growth of harmful microorganisms, ensuring food safety and quality.

InChI:InChI=1/C20H26O3/c1-5-18(2)8-6-13-12(11-18)10-14-16-19(13,3)9-7-15(21)20(16,4)17(22)23-14/h5,10,13-14,16H,1,6-9,11H2,2-4H3/t13-,14-,16-,18-,19-,20+/m1/s1

Upstream product

• 62994-56-3 3β-hydroxy-9β-pimara-7,15-dien-19,6β-olide 

Downstream Products

• 51226-29-0 (1S,4aR,4bR,7R,10R,10aS)-7-ethenyl-3,4,4a,4b,5,6,7,8,10,10a-decahydro-10-hydroxy-1,4a,7-trimethylphenanthren-2(1H)-one 

Relevant articles and documents

Biosynthesis of rice phytoalexin: enzymatic conversion of 3beta-hydroxy-9beta-pimara-7,15-dien-19,6beta-olide to momilactone A.

Momilactone A, a major rice diterpene phytoalexin, could be synthesized by dehydrogenation at the 3-position of 3beta-hydroxy-9beta-pimara-7,15-dien-19,6beta-olide in rice leaves. The presence of 3beta-hydroxy-9beta-pimara-7,15-dien-19,6beta-olide in UV-irradiated rice leaves was confirmed by comparing the mass spectra and retention times after a GC/MS analysis of the natural and synthetic compounds. The soluble protein fraction from UV-irradiated rice leaves showed dehydrogenase activity to convert 3beta-hydroxy-9beta-pimara-7,15-dien-19,6beta-olide into momilactone A. The enzyme required NAD+ or NADP+ as a hydrogen acceptor. The optimum pH for the reaction was 8. The Km value to 3beta-hydroxy-9beta-pimara-7,15-dien-19,6beta-olide was 36 microM when NAD+ was supplied as a cofactor at a concentration of 1 mM. 3fl-Hydroxy-9beta-pimara-7,15-dien-19,6beta-olide and its dehydrogenase activity were induced in a time-dependent manner by UV irradiation.