Synonym
Crambene; NSC 321802; NSC-321802; NSC321802
IUPAC/Chemical Name
4-Pentenenitrile, 3-hydroxy-, (S)-
InChi Key
PBCLOVRWBLGJQA-RXMQYKEDSA-N
InChi Code
InChI=1S/C5H7NO/c1-2-5(7)3-4-6/h2,5,7H,1,3H2/t5-/m1/s1
SMILES Code
C=C[C@@H](O)CC#N
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
97.12
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Cao Y, Adhikari S, Clément MV, Wallig M, Bhatia M. Induction of apoptosis by crambene protects mice against acute pancreatitis via anti-inflammatory pathways. Am J Pathol. 2007 May;170(5):1521-34. PubMed PMID: 17456759; PubMed Central PMCID: PMC1854948.
2: Cao Y, Adhikari S, Ang AD, Clément MV, Wallig M, Bhatia M. Crambene induces pancreatic acinar cell apoptosis via the activation of mitochondrial pathway. Am J Physiol Gastrointest Liver Physiol. 2006 Jul;291(1):G95-G101. Epub 2006 Apr 6. PubMed PMID: 16603484.
3: Nho CW, Jeffery E. Crambene, a bioactive nitrile derived from glucosinolate hydrolysis, acts via the antioxidant response element to upregulate quinone reductase alone or synergistically with indole-3-carbinol. Toxicol Appl Pharmacol. 2004 Jul 1;198(1):40-8. PubMed PMID: 15207647.
4: Keck AS, Staack R, Jeffery EH. The cruciferous nitrile crambene has bioactivity similar to sulforaphane when administered to Fischer 344 rats but is far less potent in cell culture. Nutr Cancer. 2002;42(2):233-40. PubMed PMID: 12416265.
5: Niedoborski TE, Klein BP, Wallig MA. Rapid isolation and purification of 1-cyano-2-hydroxy-3-butene (crambene) from Crambe abyssinica seed meal using immiscible solvent extraction and high-performance liquid chromatography. J Agric Food Chem. 2001 Aug;49(8):3594-9. PubMed PMID: 11513634.
6: March TH, Jeffery EH, Wallig MA. The cruciferous nitrile, crambene, induces rat hepatic and pancreatic glutathione S-transferases. Toxicol Sci. 1998 Apr;42(2):82-90. PubMed PMID: 9579020.
