Synonym
Valilactone; (-)-Valilactone
IUPAC/Chemical Name
1-((2S,3R)-3-hexyl-4-oxooxetan-2-yl)heptan-2-yl formyl-L-valinate
InChi Key
WWGVIIVMPMBQFV-HNNZKPGWSA-N
InChi Code
InChI=1S/C22H39NO5/c1-5-7-9-11-13-18-19(28-21(18)25)14-17(12-10-8-6-2)27-22(26)20(16(3)4)23-15-24/h15-20H,5-14H2,1-4H3,(H,23,24)/t17?,18-,19+,20+/m1/s1
SMILES Code
CC(C)[C@@H](C(OC(C[C@@H]([C@H]1CCCCCC)OC1=O)CCCCC)=O)NC=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
397.56
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: Richardson RD, Ma G, Oyola Y, Zancanella M, Knowles LM, Cieplak P, Romo D, Smith JW. Synthesis of novel beta-lactone inhibitors of fatty acid synthase. J Med Chem. 2008 Sep 11;51(17):5285-96. doi: 10.1021/jm800321h. Epub 2008 Aug 19. PMID: 18710210; PMCID: PMC3172131.
2: Ma G, Zancanella M, Oyola Y, Richardson RD, Smith JW, Romo D. Total synthesis and comparative analysis of orlistat, valilactone, and a transposed orlistat derivative: Inhibitors of fatty acid synthase. Org Lett. 2006 Sep 28;8(20):4497-500. doi: 10.1021/ol061651o. PMID: 16986934.
3: Wu Y, Sun YP. An expeditious enantioselective total synthesis of valilactone. J Org Chem. 2006 Jul 21;71(15):5748-51. doi: 10.1021/jo060844m. PMID: 16839158.
4: Yoshinari K, Aoki M, Ohtsuka T, Nakayama N, Itezono Y, Mutoh M, Watanabe J, Yokose K. Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation. J Antibiot (Tokyo). 1994 Dec;47(12):1376-84. doi: 10.7164/antibiotics.47.1376. PMID: 7844032.
5: Kitahara M, Asano M, Naganawa H, Maeda K, Hamada M, Aoyagi T, Umezawa H, Iitaka Y, Nakamura H. Valilactone, an inhibitor of esterase, produced by actinomycetes. J Antibiot (Tokyo). 1987 Nov;40(11):1647-50. doi: 10.7164/antibiotics.40.1647. PMID: 3693135.
