55481-88-4

Basic information

• Product Name: MOLLUGIN
• Synonyms: MOLLUGIN;Rubimaillin;2H-Naphtho[1,2-b]pyran-5-carboxylic acid;6-hydroxy-2, 2-dimethyl-, methylester;2,2-Dimethyl-6-hydroxy-2H-naphtho[1,2-b]pyran-5-carboxylic acid methyl ester;6-Hydroxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5-carboxylic acid methyl ester;Methyl 6-hydroxy-2,2-dimethylbenzo[h]chromene-5-carboxylate;MOLLUGIN(SH)
• CAS NO: 55481-88-4
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31
• EINECS: 208-727-7
• Product Categories: reference substance;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 55481-88-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 132～134℃
• Boiling Point: 453.2 °C at 760 mmHg
• Flash Point: 167.5 °C
• Appearance: /
• Density: 1.239 g/cm³
• Vapor Pressure: 7.86E-09mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 8.40±0.40(Predicted)
• CAS DataBase Reference: MOLLUGIN(CAS DataBase Reference)
• NIST Chemistry Reference: MOLLUGIN(55481-88-4)
• EPA Substance Registry System: MOLLUGIN(55481-88-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 55481-88-4(Hazardous Substances Data)

Usage

Uses

Mollugin is an anti-tumor agent inducing apoptosis and autophagy in various cancer models.

InChI:InChI=1/C17H16O4/c1-17(2)9-8-12-13(16(19)20-3)14(18)10-6-4-5-7-11(10)15(12)21-17/h4-9,18H,1-3H3

Upstream product

• 60657-93-4 methyl 6-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo-[h]chromene-5-carboxylate 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 77060-74-3 methyl 1,4-dihydroxy-2-naphthoate 
• 1740-74-5 1,1-diethoxy-3-methyl-2-butene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 105379-29-1 methyl 1-hydroxy-4-methoxy-2-naphthoate 
• 1010732-35-0 methyl 6-(methoxymethoxy)-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate 
• 97400-66-3 methyl 6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5-carboxylate 
• 873531-15-8 1,4-dimethoxy-3-(3-methyl-but-2-enyl)-naphthalene-2-carboxylic acid methyl ester 
• 31519-22-9 1,4-dihydroxy-2-naphthoic acid 
• 763-32-6 2-methyl-1-buten-4-ol 
• 571-60-8 1,4-Dihydroxynaphthalene 
• 83697-82-9 6-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5-carboxylic acid 

Downstream Products

• 60657-93-4 methyl 6-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo-[h]chromene-5-carboxylate 

Relevant articles and documents

Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities

Novel and diverse mollugin analogues (1-12) were synthesized using PhB(OH)2/AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10-12 showed high antioxidant activities in DPPH inhibition (IC50 = 0.52-1.11 μM) compared with BHT (IC50 = 9.67 μM). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100 μg/mL. Structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR data and high-resolution mass spectrometry.

CF3-substituted mollugin 2-(4-morpholinyl)-ethyl ester as a potential anti-inflammatory agent with improved aqueous solubility and metabolic stability

Although mollugin, the main ingredient of the oriental medicinal herb Rubia cordifolia, has considerable anti-inflammatory effects, it has poor aqueous solubility as well as poor metabolic and plasma stability. To overcome these shortfalls, various mollug

Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin

Organocatalytic asymmetric epoxidation of chromenes mediated by iminium salt catalysts under non-aqueous conditions provided ees as high as 99%. Contrastingly, reaction under aqueous conditions can form the corresponding diol products with ees as high as 71%. The process has been used for the synthesis of the East African medicinal plant metabolite (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin.

Facile synthesis of mollugin by kinetic control and anti-HCV (Hepatitis C Virus) activity of its analogues

Mollugin has been reported to have various biological activities including antineoplastic, antitumor, antiviral against the hepatitis B virus, anti-aging and antimutagenic activities. An effective and concise synthesis of mollugin in two steps including kinetic control from the cheap starting material 1,4-naphthoquinone has been introduced, and mollugin derivatives thus prepared are screened for their inhibition ability against the hepatitis C virus (HCV) and the dihydrobenzochromene structure might be an additional anti-HCV agent as a new leading compound.