600-76-0

Basic information

• Product Name: brazilein
• Synonyms: Benz[b]indeno[1,2-d]pyran-9(6H)-one, 6a,7-dihydro-3,6a,10-trihydroxy-
• CAS NO: 600-76-0
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.266
• Mol File: 600-76-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 683.8°C at 760 mmHg
• Flash Point: 264.9°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 1.24E-19mmHg at 25°C
• Refractive Index: 1.784
• PKA: 8.08±0.40(Predicted)
• CAS DataBase Reference: brazilein(CAS DataBase Reference)
• NIST Chemistry Reference: brazilein(600-76-0)
• EPA Substance Registry System: brazilein(600-76-0)

Safety Data

• Hazardous Substances Data: 600-76-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,18-20H,6-7H2

Synthetic route

(+-)-Brasilin (767259-33-6) → brazilein (600-76-0)

Conditions	Yield
With iodine In water at 20℃;	78%
Oxidation an der Luft;

(+)-(6ar,11bc)-7,11b-dihydro-indeno[2,1-c]chromene-3,6a,9,10-tetraol (474-07-7, 23221-90-1, 26138-10-3) → brazilein (600-76-0)

Conditions	Yield
With alkali Aufbewahren an der Luft;
With sodium iodate; water
With diethyl ether; ethanol; nitric acid
With ethanol; water; iodine at 60 - 70℃;
With potassium nitrite; acetic acid

ethanol (64-17-5) + (+-)-Brasilin (767259-33-6) + water (7732-18-5) + iodine (7553-56-2) → brazilein (600-76-0)

diethyl ether (60-29-7) + ethanol (64-17-5) + (+-)-Brasilin (767259-33-6) + nitric acid (7697-37-2) → brazilein (600-76-0)

aqueous brazilin → brazilein (600-76-0)

Conditions	Yield
With iodine

(+-)-Brasilin (767259-33-6) + acetic acid (64-19-7) + KNO2 → brazilein (600-76-0)

(+-)-Brasilin (767259-33-6) + sodium iodate → brazilein (600-76-0)

dimethyl sulfate (77-78-1) + brazilein (600-76-0) → 3,6A,10-trimethoxy-6a,7-dihydro-6H-indeno[2,1-c]chromen-9-one

Conditions	Yield
With potassium hydroxide

brazilein (600-76-0) → 2-(2,5-dihydroxy-phenoxymethyl)-2-hydroxy-3-(4-hydroxy-3,6-dioxo-cyclohexa-1,4-dienyl)-propionic acid

Conditions	Yield
With dihydrogen peroxide; acetic acid at 50℃;

brazilein (600-76-0) → 3,9,10-trihydroxy-7H-indeno[2,1-c]chromenylium; sulfate/s

Conditions	Yield
With sulfuric acid; acetic acid

brazilein (600-76-0) → 9,10-dihydroxy-3-methoxy-7H-indeno[2,1-c]chromenylium; sulfate

Conditions	Yield
Durch Methylierung; Anschliessend Behandeln mit Schwefelsaeure und Wasser;

brazilein (600-76-0) → 3,9,10-trihydroxy-7H-indeno[2,1-c]chromenylium; bromide

Conditions	Yield
durch aufeinanderfolgende Behandlung mit Schwefelsaeure und Bromwasserstoffsaeure;
With hydrogen bromide at 100℃; Im geschlossenen Rohr;

brazilein (600-76-0) → 3,9,10-trihydroxy-7H-indeno[2,1-c]chromenylium; chloride

Conditions	Yield
With hydrogenchloride at 100℃; Im geschlossenen Rohr;

brazilein (600-76-0) → 3,6a,9,10-tetraacetoxy-6,6a,7,11b-tetrahydro-indeno[2,1-c]chromene (2241-61-4)

Conditions	Yield
Bei der reduzierenden Acetylierung;

diazomethane (186581-53-3, 908094-01-9) + brazilein (600-76-0) → l-11b-Hydroxybrazilin Trimethyl Ether (130233-80-6)

Conditions	Yield
Multistep reaction;

dihydrogen peroxide (7722-84-1) + acetic acid (64-19-7) + brazilein (600-76-0) → 2-(2,5-dihydroxy-phenoxymethyl)-2-hydroxy-3-(4-hydroxy-3,6-dioxo-cyclohexa-1,4-dienyl)-propionic acid

sulfuric acid (7664-93-9) + brazilein (600-76-0) → 3,9,10-trihydroxy-7H-indeno[2,1-c]chromenylium; bromide

Conditions	Yield
Behandlung mit Bromwasserstoffsaeure;

hydrogen bromide (10035-10-6, 12258-64-9) + brazilein (600-76-0) → 3,9,10-trihydroxy-7H-indeno[2,1-c]chromenylium; bromide

Conditions	Yield
at 100℃; Im geschlossenen Rohr;

dimethyl sulfate (77-78-1) + brazilein (600-76-0) → 3,6A,9,10-tetramethoxy-6a,7-dihydro-6H-indeno[2,1-c]chromen-11b-ol (857551-85-0) + brazilein-trimethyl ether ; brazilein-dimethyl ether ; brazilein-mono-methyl ether

Conditions	Yield
With potassium hydroxide

dimethyl sulfate (77-78-1) + brazilein (600-76-0) → 10-hydroxy-3,6a-dimethoxy-6a,7-dihydro-6H-indeno[2,1-c]chromen-9-one + brazilein-trimethyl ether ; tetramethyldihydrobrasileinol; brazileinmonomethyl ether

Conditions	Yield
With potassium hydroxide

brazilein (600-76-0) → compound C22H18O7 + brazilin tetraacetate

Conditions	Yield
Gleichzeitige Acetylierung und Reduktion;

acetic acid (64-19-7) + brazilein (600-76-0) + zinc dust → compound C24H20O8

Conditions	Yield
Acetylierung des Reaktionsprodukts mit Essigsaeureanhydrid und Natriumacetat;

hydrogenchloride (7647-01-0) + brazilein (600-76-0) → isobrazilein chloride

Conditions	Yield
at 100℃; Im geschlossenen Rohr;

sulfuric acid (7664-93-9) + brazilein (600-76-0) → isobrazilein disulfate

dimethyl sulfate (77-78-1) + brazilein (600-76-0) + KOH-solution → brazileinmonomethyl ether + brazileindimethyl ether + brazileintrimethyl ether + tetramethyldihydrobrasileinol

sodium acetate (127-09-3) + acetic anhydride (108-24-7) + brazilein (600-76-0) → triacetate of brazilein(?)

acetic anhydride (108-24-7) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) + brazilein (600-76-0) + zinc dust → triacetate of brazilein(?)

propionyl chloride (79-03-8) + brazilein (600-76-0) → C22H20O7 (1215097-53-2) + C25H24O8 (1215097-52-1)

Conditions	Yield
With pyridine

Upstream product

• 767259-33-6 (+-)-Brasilin 
• 64-19-7 acetic acid 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 7697-37-2 nitric acid 
• 7732-18-5 water 
• 7553-56-2 iodine 
• 474-07-7 (+)-(6ar,11bc)-7,11b-dihydro-indeno[2,1-c]chromene-3,6a,9,10-tetraol 

Downstream Products

• 1215097-54-3 C₃₇H₂₄O₈ 
• 1215097-61-2 C₃₀H₂₄O₅ 
• 2241-61-4 (+/-)-Brasilin-tetraacetat 

Relevant articles and documents

Antitumor agents. 271: Total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents

The first total synthesis of the naturally occurring tetracyclic homoisoflavonoid brazilein (1) and 14 new analogs (1a-n) is reported. Target compounds and intermediates were assayed for anti-inflammatory effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB, and for cytotoxic activity against nasopharyngeal (KB), vincristine-resistant nasopharyngeal (KBvin), lung (A549) and prostate (DU-145) human cancer cell lines. The most active compound 1b showed potent effects on superoxide anion generation and elastase release with IC50 values of 1.2 and 1.9 μM, respectively, and was 65 times more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in the latter assay. Additionally, 1b exhibited broad spectrum in vitro anticancer activity with IC50 values of 6-11 μM against the four tested cancer cell lines.