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(+)-Griseofulvin

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Name

(+)-Griseofulvin

EINECS 204-767-4
CAS No. 126-07-8 Density 1.38 g/cm3
PSA 71.06000 LogP 2.81030
Solubility practically insoluble in water Melting Point 218-220 °C(lit.)
Formula C17H17ClO6 Boiling Point 570.4 °C at 760 mmHg
Molecular Weight 352.771 Flash Point 228 °C
Transport Information N/A Appearance crystalline solid
Safety 53-22-36/37/39-45 Risk Codes 60-61-40-43-45
Molecular Structure Molecular Structure of 126-07-8 ((+)-Griseofulvin) Hazard Symbols ToxicT,HarmfulXn
Synonyms

Spiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione,7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S-trans)-;7-Chloro-2',4,6-trimethoxy-6'b-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione;Amudane;Curling factor;Fulcin;Fulvicin;Fulvicin P/G;Fulvicin U/F;Fulvidex;Fulvina;Fulvinil;Fulvistatin;Gricin;Grifulin;Grifulvin;Gris-PEG;Grisactin;Grisefulin;Griseofulvin, (+)-;Grisofulvin;Grisovin;Grysio;Idifulvin;Likuden;Polygris;Poncyl;Spirofulvin;Xuanjing;

Article Data 7

(+)-Griseofulvin Synthetic route

136616-32-5

2'-hydroxygriseofulvin

126-07-8

griseofulvin

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;95%
469-54-5

(2S,2'R)-7-chloro-4,6-dimethoxy-2'-methyl-3H-spiro[benzofuran-2,1'-cyclohexane]-3,4',6'-trione

A

469-51-2, 469-52-3, 17818-12-1

(2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1'-(4'-methoxy-6'-methylcyclohex-3'-ene-2'-one)

B

126-07-8

griseofulvin

Conditions
ConditionsYield
With diethyl ether
67-56-1

methanol

A

469-51-2, 469-52-3, 17818-12-1

(2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1'-(4'-methoxy-6'-methylcyclohex-3'-ene-2'-one)

B

126-07-8

griseofulvin

Conditions
ConditionsYield
With hydrogenchloride

A

86549-08-8, 86562-90-5

(-)-2',3'-dihydrodehydrogriseofulvin

B

126-07-8

griseofulvin

Conditions
ConditionsYield
With selenium(IV) oxide In tert-butyl alcohol for 10h; Heating;
Conditions
ConditionsYield
Product distribution; microbal transformation by seven streptomyces species;
3573-90-8

(-)-dehydrogriseofulvin

126-07-8

griseofulvin

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; pH 7.0 phosphate buffer; Streptomyces cinereocrocatus cell-free culture; NADPH In water; acetone at 28℃; for 5h; Product distribution; effect of NADH/NADPH ratio;
7776-77-4

(+/-)-dehydrogriseofulvin

126-07-8

griseofulvin

Conditions
ConditionsYield
In water; acetone at 28℃; for 72h; Streptomyces cinereocrocatus NRRL 3443;
Conditions
ConditionsYield
Product distribution; microbal transformation by seven streptomyces species;
norgriseofulvinic acid

norgriseofulvinic acid

A

469-51-2, 469-52-3, 17818-12-1

(2S,6'R)-(7-chloro-4,6-dimethoxy-benzofuran-3-on)-2-spiro-1'-(4'-methoxy-6'-methylcyclohex-3'-ene-2'-one)

B

126-07-8

griseofulvin

Conditions
ConditionsYield
With diethyl ether

(+)-Griseofulvin Chemical Properties

Molecular Structure:
Molecular Formula: C17H17ClO6
Molecular Weight: 352.7663
IUPAC Name: (2S,5'R)-7-Chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
Synonyms of Griseofulvin (CAS NO.126-07-8): Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S,6'R)- ; Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (1'S-trans)- ; Griseofulvin [USAN:INN:BAN:JAN] ; Fulvidex (Veterinary)
CAS NO: 126-07-8
Classification Code: Agricultural Chemical ; Anti-Infective Agents ; Antibiotics, antifungal ; Antifungal ; Antifungal Agents ; Drug / Therapeutic Agent ; Fungicide, bactericide, wood preservative ; Mutation data ; Natural Product ; Reproductive Effect ; Tumor data
Melting point: 218-220 °C 
Index of Refraction: 1.583
Molar Refractivity: 85.27 cm3
Molar Volume: 255.1 cm3
Surface Tension: 52.5 dyne/cm
Density: 1.38 g/cm3
Flash Point: 228 °C
Enthalpy of Vaporization: 85.55 kJ/mol
Boiling Point: 570.4 °C at 760 mmHg
Vapour Pressure: 5.07E-13 mmHg at 25°C

(+)-Griseofulvin Uses

 Griseofulvin (CAS NO.126-07-8) is used both in animal and in humans, to treat rigworm infections of the skin and nails. It is used for the variety of goods to inhibit dermatophytes, including Paper Table is Trichophyton mentagrophytes, Trichophyton mentagrophytes Paper is a small genus spores. Right from tinea versicolor, a white beads containing bacteria and bacterial invalid. Inhibitory effect of the goods, to the vigorous growth of fungal effective. The sensitive goods for tinea capitis caused by fungi, onychomycosis, Diez watts ringworm, tinea pedis objects and body ringworm.

(+)-Griseofulvin Production

 Griseofulvin (CAS NO.126-07-8) was ousted Penicillium (Penicilli-um griseofulvum) Training fermentation liquid extraction system of antibiotics.

(+)-Griseofulvin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 280mg/kg (280mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 44, 1960.
mouse LD50 oral > 50gm/kg (50000mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 44, 1960.
mouse LD50 subcutaneous > 12gm/kg (12000mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 44, 1960.
rat LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 44, 1960.
rat LD50 intravenous 400mg/kg (400mg/kg) BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Nature. Vol. 182, Pg. 1320, 1958.
rat LD50 oral > 10gm/kg (10000mg/kg)   Drugs in Japan Vol. 6, Pg. 215, 1982.

(+)-Griseofulvin Consensus Reports

IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 10 , 1976,p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.

(+)-Griseofulvin Safety Profile

Hazard Codes of Griseofulvin (CAS NO.126-07-8): ToxicT,HarmfulXn
Risk Statements: 60-61-40-43-45 
R60: May impair fertility. 
R61: May cause harm to the unborn child. 
R40: Limited evidence of a carcinogenic effect. 
R43: May cause sensitization by skin contact. 
R45: May cause cancer.
Safety Statements: 53-22-36/37/39-45 
S53: Avoid exposure - obtain special instructions before use. 
S22: Do not breathe dust. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: WG9800000
Confirmed carcinogen with experimental neoplastigenic and teratogenic data. Poison by intravenous and intraperitoneal routes. Moderately toxic by subcutaneous route. Human mutation data reported. Experimental reproductive effects. Used as an antibiotic, pharmaceutical, and veterinary drug. When heated to decomposition it emits toxic fumes of Cl.

(+)-Griseofulvin Specification

Precautions: Keep away from heat. Keep away from sources of ignition. Do not ingest. Do not breathe dust. Wear suitable protective clothing. If ingested, seek medical advice immediately and show the container or the label. Keep away from incompatibles such as oxidizing agents.
Storage: Keep container tightly closed. Keep container in a cool, well-ventilated area.

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