33390-21-5

Basic information

• Product Name: bikaverin
• Synonyms: bikaverin;1-Methyl-3,8-dimethoxy-6,11-dihydroxy-12H-benzo[b]xanthene-7,10,12-trione;6,11-Dihydroxy-3,8-dimethoxy-1-methyl-10H-benzo[b]xanthene-7,10,12-trione;Lycopersin;NSC 215139;6,11-Dihydroxy-3,8-dimethoxy-1-methylbenzo[b]xanthene-7,10, 12-trione
• CAS NO: 33390-21-5
• Molecular Formula: C20H14O8
• Molecular Weight: 382.323
• Mol File: 33390-21-5.mol

Chemical Properties

• Melting Point: >322℃
• Boiling Point: 429.5°C (rough estimate)
• Flash Point: 263.3°C
• Appearance: /
• Density: 1.3545 (rough estimate)
• Vapor Pressure: 2.07E-21mmHg at 25°C
• Refractive Index: 1.4430 (estimate)
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble0.5mg/mL (may require sonication and heating)
• CAS DataBase Reference: bikaverin(CAS DataBase Reference)
• NIST Chemistry Reference: bikaverin(33390-21-5)
• EPA Substance Registry System: bikaverin(33390-21-5)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• RTECS: DM2901000
• Hazardous Substances Data: 33390-21-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Bikaverin is used as an antibiotic agent for its ability to inhibit bacterial growth, making it a valuable component in the development of new antibiotics to combat resistant strains.
Used in Antifungal Applications:
Bikaverin is used as an antifungal agent to treat various fungal infections due to its ability to inhibit fungal growth and prevent the spread of infections.
Used in Anticancer Applications:
Bikaverin is used as an anticancer agent, potentially targeting and inhibiting the growth of cancer cells through its interaction with High Affinity Binding Protein (HABP). This property makes it a promising candidate for further research and development in the field of oncology.
Used in Drug Delivery Systems:
Bikaverin's potential as an inhibitor of HABP may also be utilized in the development of novel drug delivery systems, where it could be employed to enhance the targeting and efficacy of anticancer drugs, improving their bioavailability and therapeutic outcomes.

InChI:InChI=1/C20H14O8/c1-7-4-8(26-2)5-10-12(7)17(23)15-18(24)13-9(21)6-11(27-3)16(22)14(13)19(25)20(15)28-10/h4-6,24-25H,1-3H3

Upstream product

• 33390-22-6 norbikaverin 
• 74-88-4 methyl iodide 
• 122182-23-4 2-(benzyloxy-4-methoxy-6-methylbenzoyl)-1,4,5,6,8-pentamethoxynaphthalene 
• 36440-12-7 2-hydroxy-5,7-dimethoxy-1,4-naphthoquinone 
• 65565-48-2 2-chloro-5,7-dimethoxy-1,4-naphthoquinone 
• 122182-25-6 2,3-dihydro-5,8-dihydroxy-6,6-dimethoxy-4'-methylnaphthalene-2-spiro-2'-2'H-benzofuran-1,3',4-trione 
• 83375-27-3 11-hydroxy-3,8,10-trimethoxy-1-methyl-12H-benzoxanthen-12-one 
• 33390-24-8 Bikaverine dimethylether 
• 122182-24-5 6-(2-benzyloxy-4-methoxy-6-methylbenzoyl)2,5,8-trimethoxy-1,4-naphthoquinone 
• 122182-21-2 1,2,4,5,8-pentamethoxynaphthalene 
• 23149-34-0 5,6-dibromo-1,2,4-trimethoxybenzene 
• 65857-84-3 8,10-bis(benzyloxy)-3-methoxy-1-methylbenzoxanthen-6,11,12-trione 
• 65857-78-5 methyl 2-acetyl-3,5-bis(benzyloxy)phenylacetate 
• 71741-18-9 6,8-Bis-benzyloxy-naphthalene-1,3-diol 

Relevant articles and documents

Regiospecific synthesis of bikaverin

A regiospecific synthesis of bikaverin (1) is described starting from methyl 2-hydroxy-4-methoxy-6-methyl benzoate (2) and 2-chloro-5,7-dimethoxy-1,4-naphthoquinone (4).

New total synthesis of bikaverin

On the basis of non-catalysed thermal condensation of a Mannich based with a phenol, followed by dehydration to an o.quinonic chromene further isomerized to a p.quinonic one, the synthesis of bikaverin 7 has been achieved via a six-step route involving selective dealkylation of bikaverin-dimethylether 6.

CONVENIENT SYNTHESES OF THE NATURALLY OCCURRING BENZOXANTHEN-12-ONE BIKAVERIN. X-RAY CRYSTALLOGRAPHIC CONFIRMATION OF THE PRODUCT REGIOCHEMISTRY

The synthesis of bikaverin (6,11-dihydroxy-3,8-dimethoxy-1-methylbenzoxanthene-7,10,12-trione) (1) by two related routes is reported.Key steps include the formation of 1,2,4,5,8-pentamethoxynaphthalene (4) in good yield and its regiospecific acylation

A Synthesis of Bikaverin (7,12-Dihydro-6,11-dihydroxy-3,8-dimethoxy-1-methyl-10H-benzoxanthene-7,10,12-trione) and some Related Benzoxanthones and Quinones

Bikaverin, a biologically interesting fungal pigment with the highly oxidised benzoxanthone structure (1), has been synthesized in two steps from 2-hydroxy-4-methoxy-6-methylacetophenone (6f) and dimethyl 3,5-dimethoxyhomophthalate (7f).The synthesis invo

Synthesis of Bikaverin

The total synthesis of bikaverin (1b) is described, from everninic acid (5) and 3,5-dihydrobenzoic acid (6).Dieckmann condensation of methyl 2-acetyl-3,5-bis(benzyloxy)phenylacetate (14), synthesised from (6), followed by treatment with protected everninic acid chloride (9) gave 1,3-bisbenzyloxy-6,8-bis(2-benzyloxy-4-methoxy-6-methylbenzyloxy)naphthalene (16).Photoinduced Fries rearrangement of (16) afforded 1,3-bis(benzyloxy)-7-(2-benzyloxy-4-methoxy-6-methylbenzoyl)-6-(2-benzyloxy-4-methoxy-6-methylbenzoyloxy)-8-hydroxynaphthalene (23).Ring closure of (23) with tetramethylammonium hydroxide in pyridine gave the angular benzoxanthene, 1,3-bis(benzyloxy-6-hydroxy)-10-methoxy-8-methylbenzoxanthen-7-one (25), which was oxidized with potassium dichromate to give the orthoquinone, 1,3-bis(benzyloxy)-10-methoxy-8-methylbenzoxanthen-5,6,7-trione (28).By a novel type of rearrangement, (28) was transformed into the linear benzoxanthen, 8,10-bis(benzyloxy)-3-methoxy-1-methylbenzoxanthen-6,11,12-trione (29) by treatment with silica gel.Oxidation and debenzylation of (29) with manganese dioxide in concentrated H2SO4 gave norbikaverin (1a).