Synonym
Julocrotine; Julocrotonine; Julocrotine, (-)-;
IUPAC/Chemical Name
(S)-N-((S)-2,6-dioxo-1-phenethylpiperidin-3-yl)-2-methylbutanamide
InChi Key
ASALPLLZVFIFMF-ZFWWWQNUSA-N
InChi Code
InChI=1S/C18H24N2O3/c1-3-13(2)17(22)19-15-9-10-16(21)20(18(15)23)12-11-14-7-5-4-6-8-14/h4-8,13,15H,3,9-12H2,1-2H3,(H,19,22)/t13-,15-/m0/s1
SMILES Code
CC[C@H](C)C(N[C@@H](CC1)C(N(CCC2=CC=CC=C2)C1=O)=O)=O
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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
316.40
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: Ndunda B, Langat MK, Wanjohi JM, Midiwo JO, Kerubo LO. Alienusolin, a new 4α-deoxyphorbol ester derivative, and crotonimide C, a new glutarimide alkaloid from the Kenyan Croton alienus. Planta Med. 2013 Dec;79(18):1762-6. doi: 10.1055/s-0033-1351044. Epub 2013 Dec 19. PubMed PMID: 24356872.
2: Neves Filho RA, Westermann B, Wessjohann LA. Synthesis of (-)-julocrotine and a diversity oriented Ugi-approach to analogues and probes. Beilstein J Org Chem. 2011;7:1504-7. doi: 10.3762/bjoc.7.175. Epub 2011 Nov 7. PubMed PMID: 22238524; PubMed Central PMCID: PMC3252850.
3: Silva LL, Joussef AC. Synthesis of N-[(3S)-2,6-dioxo-1-(2-phenylethyl)-3-piperidinyl]-(2S)-2-methylbutanamide ((-)-julocrotine). J Nat Prod. 2011 Jun 24;74(6):1531-4. doi: 10.1021/np200234e. Epub 2011 May 5. PubMed PMID: 21545108.
4: Guimarães LR, Rodrigues AP, Marinho PS, Muller AH, Guilhon GM, Santos LS, do Nascimento JL, Silva EO. Activity of the julocrotine, a glutarimide alkaloid from Croton pullei var. glabrior, on Leishmania (L.) amazonensis. Parasitol Res. 2010 Oct;107(5):1075-81. doi: 10.1007/s00436-010-1973-0. Epub 2010 Jul 27. PubMed PMID: 20661748.
5: Aboagye FA, Sam GH, Massiot G, Lavaud C. Julocrotine, a glutarimide alkaloid from Croton membranaceus. Fitoterapia. 2000 Aug;71(4):461-2. PubMed PMID: 10925028.
6: Vallejos RH, Andreo CS. Alkaloids as inhibitors of photophosphorylation in spinach chloroplasts. Biochim Biophys Acta. 1974 Jan 18;333(1):141-8. PubMed PMID: 19397001.
