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[ CAS No. 497-30-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 497-30-3
Chemical Structure| 497-30-3
Structure of 497-30-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 497-30-3 ]

CAS No. :497-30-3 MDL No. :MFCD00167474
Formula : C9H15N3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :SSISHJJTAXXQAX-ZETCQYMHSA-N
M.W : 229.30 Pubchem ID :5351619
Synonyms :
L-(+)-Ergothioneine;2-Mercaotohistidine Betaine;L-Ergothioneine;NSC 7175

Calculated chemistry of [ 497-30-3 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.56
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.18
TPSA : 103.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : -2.09
Log Po/w (XLOGP3) : -0.3
Log Po/w (WLOGP) : -0.56
Log Po/w (MLOGP) : -4.29
Log Po/w (SILICOS-IT) : 1.88
Consensus Log Po/w : -1.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.06
Solubility : 20.2 mg/ml ; 0.088 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 8.72 mg/ml ; 0.038 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.4
Solubility : 0.917 mg/ml ; 0.004 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.8

Safety of [ 497-30-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 497-30-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 497-30-3 ]

[ 497-30-3 ] Synthesis Path-Downstream   1~2

  • 2
  • potassium thiocyanate [ No CAS ]
  • C8H16N2O3 [ No CAS ]
  • [ 497-30-3 ]
YieldReaction ConditionsOperation in experiment
1.1 g L-Ergothioneine (E) (0137) The solution of compound D (approximately 11 mmol) from step 2 was warmed to 85-90 C. and 5 g of KCNS in 10 mL water was added. This solution was stirred in a water bath at 85-90 C. for 1-2 hours. (0138) When reaction progress was complete by HPLC, this solution was cooled to approximately 30 C. Approximately 15 mL of concentrated HCl in 15 mL of water was added, and this acidic solution was evaporated (bath 30 C., vacuum). The residue was dissolved in 20 mL ethanol (200 proof) and was again evaporated. 30 mL ethanol (200 proof) was added. For a few minutes this mixture was stirred on bath at 30 C., and then cooled for 20 min on ice. The salts were filtered off and washed with 20 mL of ethanol (200 proof) and the filtrates were basified with a dilute solution of LiOH to pH 3.6-4 by pH meter. (0139) After total evaporation under vacuum in order to remove water, the residue was stirred on RVE overnight with 30 mL ethanol. Then the solid was filtered, washed with 2×5 mL ethanol and dried. Approximately 0.8 g of solid crystalline L-ergothioneine was obtained. Analysis by HPLC showed approximately 85% pure product. Optical rotation was approximately 80-90, and the color was light brown. From mother liquors, an additional 0.3 g was obtained, for a total 1.1 g (43%) of L-ergothioneine. (0140) The yield of L-ergothioneine (E) from hercynine (A) is approximately 40-50%.
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