ChemicalBook > CAS DataBase List > Validamycin

Validamycin

Product Name
Validamycin
CAS No.
37248-47-8
Chemical Name
Validamycin
Synonyms
VALIDAMYCIN A;MYCIN;valimon;SOLACOL;t-7545-a;VALIDACIN;VALIDAMYCIN;VALDIDAMYCIN;jiangonmycin;Validacin[R]
CBNumber
CB7236710
Molecular Formula
C20H35NO13
Formula Weight
497.49
MOL File
37248-47-8.mol
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Validamycin Property

Melting point:
130-135°C
alpha 
D24 +110° (c = 1 in water or pyridine), +92° (c = 1 in DMF)
Boiling point:
813.7±65.0 °C(Predicted)
Density 
1.69±0.1 g/cm3(Predicted)
vapor pressure 
Neglible at room temperature
storage temp. 
0-6°C
solubility 
DMSO: 2 mg/ml; PBS (pH 7.2): 10 mg/ml
form 
Liquid
Water Solubility 
Readily soluble
pka
6.0(at 25℃)
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Safety

Hazardous Substances Data
37248-47-8(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H227Combustible liquid

Precautionary statements

P403+P235Store in a well-ventilated place. Keep cool.

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N-Bromosuccinimide Price

Alfa Aesar
Product number
J67357
Product name
Validamycin A, 100 mg/ml in DMSO
Purity
sterile-filtered
Packaging
1ml
Price
$40.8
Updated
2021/12/16
Alfa Aesar
Product number
J67357
Product name
Validamycin A, 100 mg/ml in DMSO
Purity
sterile-filtered
Packaging
5x1ml
Price
$153
Updated
2021/12/16
Cayman Chemical
Product number
15326
Product name
Validamycin A
Purity
≥60%
Packaging
500mg
Price
$46
Updated
2024/03/01
Cayman Chemical
Product number
15326
Product name
Validamycin A
Purity
≥60%
Packaging
1g
Price
$79
Updated
2024/03/01
Cayman Chemical
Product number
15326
Product name
Validamycin A
Purity
≥60%
Packaging
25mg
Price
$48
Updated
2023/06/20
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Validamycin Chemical Properties,Usage,Production

Description

Validamycin A is produced by the fermentation of Streptomyces hygroscopicus var. limoneus nov. var (30). Structure revised (31). Colorless, odorless, hygroscopic powder. V.p. Negligible at room temperature. Solubility: Readily soluble in water, soluble in methanol, dimethylformamide and dimethyl sulfoxide. Slightly soluble in ethanol and acetone. Sparingly soluble in diethyl ether and ethyl acetate. pKa 6.0 Stability [α]24D + 110? (water).

Uses

Validamycin A (>70%) Hydrochloride Salt is a metabolite of Validamycin A (>70%) (V943430) which is an antibiotic fungicide that inhibits trehalase activity in plants, insects, and fungi.

Uses

Validamycin A is the major analogue of a family of cyclitol disaccharides isolated from Streptomyces hygroscopicus var. limoneus by researchers at Takeda in 1970. Although commonly regarded as an aminoglycoside, validamycin shares little in common with conventional aminoglycosides such as streptomycin and gentamicin. Validamycin A is a potent antifungal agent and is used to control fungi in crop production. Validamycin A acts as a potent inhibitor of trehalase, an important enzyme in carbohydrate storage and ultilisation in fungi.

Uses

Validamycin A is used for the control of Rhizoctonia diseases in rice (sheath blight), potatoes, vegetables, strawberries, tobacco and other crops.

Definition

ChEBI: A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its beta-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cycloh x-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus.

Application

Validamycin was found in the culture broth of Streptomyces hygroscopicus var. limoneus by Takeda Chemicals Industries in 1971 in the course of screening for substances active against sheath blight in the rice plant. It consists of five components. The major component, validamycin A, was found to be the major contributor to the activity. Validamycin is active against a variety of phytopathogenic fungi, especiallyPellicularia sasakii, and it has been used to protect rice plants against sheath blight.

Pharmacology

Validamycin A specifically inhibits trehalase in R. solani AG-1 in a competitive manner between validoxylamine A (the possible active form of validamycin A) and the substrate, trehalose (33). Because trehalose is a storage carbohydrate in some fungi, trehalase is suggested to play an essential role for the digestion of trehalose to D-glucose and for its transportation to the hyphal tips (34).

Metabolic pathway

Validamycin A is an effective fungistatic (as opposed to fungicidal) antibiotic which has a very low toxicity to mammals and fish. This is presumably a consequence of its selective mode of action, the inhibition of trehalase. It is readily degraded under environmental conditions.

Degradation

Validamycin A is stable at room temperature in neutral or alkaline media but is unstable in acidic media.

Toxicity evaluation

Acute oral LD50 for rats and mice >20 g/kg. Acute percutaneous LD50 for rats >5 g/kg. Nonirritating to skin (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5 mg/L air. NOEL: In 90-d feeding trials, rats receiving 1 g/kg of diet and mice receiving 2 g/kg of diet showed no ill-effects. In 2-y feeding trials, NOEL for rats was 40.4 mg/kg daily. Toxicity Class WHO (a.i.) III; EPA (formulation) IV.

Validamycin Preparation Products And Raw materials

Raw materials

XANTHOPTERIN

Preparation Products

Imidacloprid+Validamycin+Monosultap,W.P. Validamycin aqueous solution Validamycin+Diniconazole,W.P.
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View Lastest Price from Validamycin manufacturers

Hebei Duling International Trade Co. LTD
Product
Validamycin 37248-47-8
Price
US $145.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000 tons
Release date
2023-03-21
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Validamycin 37248-47-8
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-02-06
Hebei Guanlang Biotechnology Co,.LTD
Product
Validamycin 37248-47-8
Price
US $10.70/Kg/Drum
Min. Order
10g
Purity
99%
Supply Ability
10000kg
Release date
2021-07-28

37248-47-8, ValidamycinRelated Search:

Tris(hydroxymethyl)nitromethane Valiolamine Valienamine Dianemycin 1-sodium salt Monensin Validamine D-chiro-inositol CIS-2-METHYLAMINO-CYCLOHEXANOL N-(2-HEPTYL)CYCLOHEXYLAMINE Validamycin E VALIDAMYCIN D Validamycin+Buprofenzin+Monosultap,W.P. Validamycin+Tricycloazole+Triadimefon,W.P.(16%) Validamycin+Buprofenzin+Isoprocarb,W.P.(32%) Validamycin 28% carbendazim-jingangmeisu flowable formulation Imidacloprid+Validamycin,W.P.(15%) Validamycin+Bisultap,aqueous solusion Validamycin A

  • valimon
  • VALIDACIN
  • VALIDAMYCIN
  • VALIDAMYCIN A
  • ((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-,(1s-(1-alpha,4
  • (1s-(1a,4a,5b,6a))-1,5,6-trideoxy-3-o-b-d-glucopyranosyl-5-(hydroxymethyl)-1-(
  • D-Chiro-Inositol,1,5,6-trideoxy-4-O-b-D-glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-
  • (1s-(1alpha,4alpha,5beta,6alpha))-1,5,6-trideoxy-4-o-beta-d-glucopyrano
  • (4,5,6-trihydroxy-3-(hydroxymethyl)-=2-cyclohexen-1-yl)amino)-d-chiro-inositol
  • )amino)-d-chiro-inositol
  • 1,5,6-trideoxy-3-o-.beta.-d-glucopyranosyl-5-(hydroxymethyl)-1-[[4,5,6-trihydroxy-3-(hydroxymethyl)d-Chiro-inositol
  • 1,5,6-trideoxy-3-o-beta-d-glucopyranosyl-5-(hydroxymethyl)-1-d-chiro-inosito
  • 1l-(1,3,4/2,6)-2,3-dihydroxy-6-hydroxymethyl-4-((1s,4r,5s,6s)-4,5,6-trihydroxy
  • 3,4/2,6)-2,3-dihydroxy-6-hydromethyl-4-((1s,4r,5s,6s)-4,5,6-trihydroxy-3-1l-(
  • -3-hydroxymethylcyclohex-2-enylamino)cyclohexylb-d-glucopyranoside
  • 5-beta,6-alpha))--alph
  • d-1,5,6-trideoxy-3-o-beta-d-glucopyranosyl-5-(hydroxymethyl)-1-((4,5,6-trihydr
  • hydroxymethylcyclohex-2-enylamino)cyclohexylbeta-d-glucopyranoside
  • oxy-3-(hydroxymethyl)-2-cyclohexen-1-yl)amino)-d-chiroinositol
  • syl-5-(hydroxymethyl)-1-((4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl
  • t-7545-a
  • MYCIN
  • SOLACOL
  • 2-[2,3-Dihydroxy-6-(hydroxymethyl)-4-[[4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]cyclohexoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  • jinggangmycin
  • validamycin (jmaf)
  • VALDIDAMYCIN
  • jiangonmycin
  • N-[（1S）-（1，4，6/5）-3-hydroxymethyl-4,5,6-trihydroxy-2-cyclohexenyl] [O-β-D-glucopyranosyl-(1→3)]-1S-(1,2,4/3,5)-2,3,4-trihydroxy-5-hytroxymethylcy-clohexylamine
  • 4-O-(β-D-glucopyranosyl)-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-1,5,6-trideoxy-D-chiro-inositol
  • 4-O-β-D-Glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-1,5,6-Trideoxy-D-chiro-inositol
  • Validacin[R]
  • Validamycin (Validamycin A)
  • N-[（1S）-（1,4,6
  • ValidaMycin (t
  • [1S-(1-alpha, 4-alpha, 5-beta, 6-alpha)]-1,5,6-Trideoxy-3-O-beta-D-glucopyranosyl-5-(hydroxymethyl)-1-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexene-1-yl]amino]-D-chiro inositol
  • D-chiro-Inositol, 1,5,6-trideoxy-3-O-beta-D-glucopyranosyl-
  • Validamycin (technical)
  • Validamycin POR [37248-47-8]
  • Validamycin A Standard
  • Validamycinv
  • D-chiro-Inositol, 1,5,6-trideoxy-4-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-
  • Validamycin USP/EP/BP
  • Validamycin A (>70%)
  • Validamycin AQ: What is Validamycin A Q: What is the CAS Number of Validamycin A Q: What is the storage condition of Validamycin A Q: What are the applications of Validamycin A
  • Aclarubicin Impurity 1
  • Validamycin (mixture of isomers）
  • (2R,3R,4S,5S,6R)-2-(((1R,2R,3S,4S,6R)-2,3-Dihydroxy-6-(hydroxymethyl)-4-(((1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl)amino)cyclohexyl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  • -Biphenyl]-3-yl(phenyl)methanone
  • Jinggangmycin A
  • Validamycin A in Methanol
  • 37248-47-8
  • C20H35O13N
  • C20H35NO13
  • FUNGICIDE