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CAS No.: | 481-42-5 |
---|---|
Name: | PLUMBAGIN |
Article Data: | 38 |
Molecular Structure: | |
Formula: | C11H8O3 |
Molecular Weight: | 188.183 |
Synonyms: | 2-Methyl-5-hydroxy-1,4-naphthoquinone;2-Methyljuglone;5-Hydroxy-2-methyl-1,4-naphthoquinone;NSC 688284; |
EINECS: | 207-569-6 |
Density: | 1.354 g/cm3 |
Melting Point: | 76-78 °C(lit.) |
Boiling Point: | 383.927 °C at 760 mmHg |
Flash Point: | 200.165 °C |
Appearance: | orange crystalline powder or crystals |
Hazard Symbols: | T |
Risk Codes: | 25-34 |
Safety: | 22-26-36/37/39-45 |
Transport Information: | UN 2923 8/PG 2 |
PSA: | 54.37000 |
LogP: | 1.71750 |
2-bromo-5-hydroxy-[1,4]naphthoquinone
tetramethylstannane
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0); copper(I) bromide In 1,4-dioxane for 15h; Heating; | 100% |
tetrakis(triphenylphosphine) palladium(0); copper(I) bromide In 1,4-dioxane for 15h; Heating; Yield given; |
6-methyl-5,8-dioxo-5,8-dihydronaphthalen-1-yl acetate
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 50℃; for 1h; | 100% |
5-methoxymethoxy-2-methyl-1,4-naphthoquinone
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In neat (no solvent, solid phase) at 20℃; for 0.583333h; Green chemistry; | 97% |
With hydrogenchloride In methanol for 0.0833333h; Heating; | 95% |
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
With cerium(IV) ammonium sulphate In water; acetonitrile for 0.25h; Cooling with ice; | 95% |
With ammonium cerous sulfate In water; acetonitrile at 0℃; for 0.25h; | 95% |
2-methyl-5-methoxy-1,4-naphthoquinone
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
With aluminium trichloride | 90% |
With aluminium trichloride In dichloromethane 1.) 1 h, room temp., 2.) 15 min, water; | 90% |
With aluminium trichloride In dichloromethane at 20℃; for 2h; | 75% |
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 15h; Ambient temperature; | 82% |
2-Methyl-1,5-naphthalindiol-5-acetat
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
With oxygen; methylene blue In methanol at 20℃; for 4h; Irradiation; | 69% |
Multi-step reaction with 2 steps 1: 74 percent / aq. ON(SO3K)2, KH2PO4 / methanol / 2 h 2: 100 percent / conc. HCl / methanol / 1 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; trifluoroacetic acid; trifluoroacetic anhydride; bis-[(trifluoroacetoxy)iodo]benzene at 80℃; for 12h; Sealed tube; chemoselective reaction; | 61% |
With ammonium peroxydisulfate; sulfuric acid |
5-acetyloxy-3-bromo-2-methyl-1,4-naphthoquinone
5-hydroxy-2-methyl-1,4-naphthoquinone
Conditions | Yield |
---|---|
at 145℃; for 12h; | 60% |
1,8-Dihydroxy-3-methylnaphthalin
A
5-hydroxy-2-methyl-1,4-naphthoquinone
B
7-methyljuglone
Conditions | Yield |
---|---|
With salcomine; oxygen In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; | A 51% B 30% |
The Plumbagin, with the CAS registry number 481-42-5, is also known as 2-Methyl-5-hydroxy-1,4-naphthalenedione. It belongs to the product category of Anthraquinones, Hydroquinones and Quinones. Its EINECS registry number is 207-569-6. This chemical's molecular formula is C11H8O3 and molecular weight is 188.18. What's more, both its IUPAC name and systematic name are the same which is called 5-Hydroxy-2-methylnaphthalene-1,4-dione. Plumbagin is a yellow dye, formally derived from naphthoquinone. It is regarded as a toxin. And this chemical is used as dye intermediates.
Physical properties about Plumbagin are: (1)ACD/LogP: 2.45; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.42; (4)ACD/LogD (pH 7.4): 1.67; (5)ACD/BCF (pH 5.5): 40.04; (6)ACD/BCF (pH 7.4): 7.06; (7)ACD/KOC (pH 5.5): 479.8; (8)ACD/KOC (pH 7.4): 84.56; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.63; (14)Molar Refractivity: 49.48 cm3; (15)Molar Volume: 138.9 cm3; (16)Surface Tension: 57.1 dyne/cm; (17)Density: 1.354 g/cm3; (18)Flash Point: 200.2 °C; (19)Enthalpy of Vaporization: 65.73 kJ/mol; (20)Boiling Point: 383.9 °C at 760 mmHg; (21)Vapour Pressure: 1.92E-06 mmHg at 25 °C.
When you are dealing with this chemical, you should be very careful. It is toxic if swallowed and it may cause burns. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell seek medical advice immediately.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C\2c1c(O)cccc1C(=O)/C(=C/2)C
(2) InChI: InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
(3) InChIKey: VCMMXZQDRFWYSE-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 5mg/kg (5mg/kg) | "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 73, 1982. | |
mouse | LD50 | intravenous | 7990ug/kg (7.99mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 48, Pg. 1128, 1996. Link to PubMed | |
mouse | LD50 | oral | 16mg/kg (16mg/kg) | Indian Journal of Experimental Biology. Vol. 18, Pg. 876, 1980. Link to PubMed | |
rat | LD50 | oral | 65mg/kg (65mg/kg) | Indian Journal of Medical Research. Vol. 65, Pg. 829, 1977. |