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A1404950

Veratramine , ≥98% , 60-70-8

CAS NO.:60-70-8

Empirical Formula: C27H39NO2

Molecular Weight: 409.6

MDL number: MFCD00468124

Pack Size Price Stock Quantity
1mg RMB39.20 In Stock
5mg RMB63.20 In Stock
10mg RMB95.20 In Stock
25mg RMB156.80 In Stock
50mg RMB279.20 In Stock
100mg RMB457.60 In Stock
250mg RMB759.20 In Stock
1g RMB1903.20 In Stock
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Update time: 2022-07-08

PRODUCT Properties

Melting point: 122-1240C
alpha  D25 -71.8° (c = 1.21); D25 -70° (c = 1.56 in methanol)
Boiling point: 529.83°C (rough estimate)
Density  1.0393 (rough estimate)
refractive index  1.6400 (estimate)
storage temp.  Sealed in dry,Store in freezer, under -20°C
solubility  Soluble in DMSO (up to 12 mg/ml) or in Ethanol (up to 10 mg/ml)
form  solid
pka 14.82±0.60(Predicted)
color  Tan
λmax 268nm(lit.)
Merck  14,9952
Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
CAS DataBase Reference 60-70-8

Description and Uses

This alkaloid occurs naturally in Veratrum grandi/lorum and V. viride and is also formed during the hydrolysis of Veratrosine (q.v.). It forms colourless crystals of the monohydrate from aqueous EtOH and has [α]19D - 70° (MeOH). The hydrochloride forms colourless plates from EtOH, m.p. 20l-2°C and the picrate, yellow plates, m.p. 217.5 - 218°C. Two non-phenolic hydroxyl groups and an imino group are present and the triacetyl derivative, m.p. 205.5-206°C; [α]14.5D + 37.8° (MeOH), on controlled hydrolysis furnishes the N-acetyl com_x0002_pound, m.p. 176-8°C. The O-acetate has also been prepared as colourless prisms from aqueous EtOH, m.p. 20l-2°C but it is still uncertain which of the hydroxyl groups is acetylated in this derivative. Treatment with methyl iodide in MeOH in the presence of sodium carbonate gives N-methylveratraminc methiodide, m.p. 268°C (dec.) from which the methochloride, m.p. 277°C can be obtained. On catalytic hydrogenation, the base furnishes the dihydro derivative, m.p. 198- 200°C; [α]27D + 27.4°, which forms the N-acetyl compound, m.p. 220-3°C; [α]28D + 81° and the triacetyl derivative, m.p. l89.5-190.5°C; [α]24D + 84°.

The hedgehog (Hh) signaling pathway, which is blocked by cyclopamine , plays a key role in morphogenesis and has potential applications in the treatment of cancer. Veratramine, a teratogenic steroidal alkaloid isolated from the corn lily (Veratrum sp.), is an analog of cyclopamine that can inhibit the Hh signaling-dependent proliferation of NIH/3T3 cells at 8 μM. Additionally, veratramine has anti-thrombotic activity as it dose dependently inhibits platelet aggregation in rabbits ex vivo. While it may be most useful as a signal transduction inhibitor for treating tumors, veratramine also induces serotonin release and inhibits its re-uptake in the CNS.

Safety

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P501-P270-P264-P301+P310+P330-P405
RIDADR  UN 2811 6.1/PG III
RTECS  YX5094000
HS Code  2933.39.4100
HazardClass  6.1
PackingGroup  III
Hazardous Substances Data 60-70-8(Hazardous Substances Data)

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