Decarestrictine D | CAS#: 127393-89-9 | Hypolipidemic

MedKoo Cat#: 582003 | Name: Decarestrictine D

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Decarestrictine D is a 10-membered lactone which potently inhibits cholesterol biosynthesis and shows hypolipidemic activity.

Chemical Structure

Decarestrictine D

CAS#127393-89-9

Theoretical Analysis

MedKoo Cat#: 582003

Name: Decarestrictine D

CAS#: 127393-89-9

Chemical Formula: C10H16O5

Exact Mass: 216.1000

Molecular Weight: 216.23

Elemental Analysis: C, 55.55; H, 7.46; O, 36.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Decarestrictine D; SM 133; Tuckolide; Decarestrictin D; decarestrictine D; Decarestrictine D (Tuckolide)

IUPAC/Chemical Name

(4S,5S,8S,10R,E)-4,5,8-trihydroxy-10-methyl-3,4,5,8,9,10-hexahydro-2H-oxecin-2-one

InChi Key

HWMMWMJBUOCCFZ-XYEXOTNWSA-N

InChi Code

InChI=1S/C10H16O5/c1-6-4-7(11)2-3-8(12)9(13)5-10(14)15-6/h2-3,6-9,11-13H,4-5H2,1H3/b3-2+/t6-,7-,8+,9+/m1/s1

SMILES Code

O1C(C[C@@H]([C@H](C=C[C@H](C[C@H]1C)O)O)O)=O

Appearance

Solid powder

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 216.23 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: Binanzer M, Fang GY, Aggarwal VK. Asymmetric synthesis of allylsilanes by the borylation of lithiated carbamates: formal total synthesis of (-)-decarestrictine D. Angew Chem Int Ed Engl. 2010 Jun 7;49(25):4264-8. doi: 10.1002/anie.201001223. PubMed PMID: 20446329. 2: Sy AA, Swenson DC, Gloer JB, Wicklow DT. Botryolides A-E, decarestrictine analogues from a fungicolous Botryotrichum sp. (NRRL 38180). J Nat Prod. 2008 Mar;71(3):415-9. doi: 10.1021/np070610d. Epub 2007 Dec 30. PubMed PMID: 18163662. 3: Kobayashi Y, Yoshida S, Asano M, Takeuchi A, Acharya HP. Nickel-catalyzed coupling producing (2Z)-2,4-alkadien-1-ols, conversion to (E)-3-alkene-1,2,5-triol derivatives, and synthesis of decarestrictine D. J Org Chem. 2007 Mar 2;72(5):1707-16. Epub 2007 Jan 25. PubMed PMID: 17253757. 4: Kobayashi Y, Asano M, Yoshida S, Takeuchi A. Stereoselective synthesis of decarestrictine D from a previously inaccessible (2Z,4E)-alkadienyl alcohol precursor. Org Lett. 2005 Apr 14;7(8):1533-6. PubMed PMID: 15816745. 5: Colle S, Taillefumier C, Chapleur Y, Liebl R, Schmidt A. Synthesis and biological testings as inhibitors of HMGCoA reductase of the seco-acid of tuckolide and its C-7 epimer. Bioorg Med Chem. 1999 Jun;7(6):1049-57. PubMed PMID: 10428373. 6: Andrus MB, Shih TL. Synthesis of Tuckolide, a New Cholesterol Biosynthesis Inhibitor. J Org Chem. 1996 Dec 13;61(25):8780-8785. PubMed PMID: 11667854. 7: Mayer M, Thiericke R. A non-enzymatic reaction in the late biosynthesis of the decarestrictine family. J Antibiot (Tokyo). 1993 Sep;46(9):1372-80. PubMed PMID: 8226316. 8: Ayer WA, Sun M, Browne LM, Brinen LS, Clardy J. Chemical investigation of the metabolites from the Canadian tuckahoe, Polyporus tuberaster. J Nat Prod. 1992 May;55(5):649-53. PubMed PMID: 1517736. 9: Göhrt A, Zeeck A, Hütter K, Kirsch R, Kluge H, Thiericke R. Secondary metabolites by chemical screening. 9. Decarestrictines, a new family of inhibitors of cholesterol biosynthesis from Penicillium. II. Structure elucidation of the decarestrictines A to D. J Antibiot (Tokyo). 1992 Jan;45(1):66-73. PubMed PMID: 1548191. 10: Grabley S, Granzer E, Hütter K, Ludwig D, Mayer M, Thiericke R, Till G, Wink J, Philipps S, Zeeck A. Secondary metabolites by chemical screening. 8. Decarestrictines, a new family of inhibitors of cholesterol biosynthesis from Penicillium. I. Strain description, fermentation, isolation and properties. J Antibiot (Tokyo). 1992 Jan;45(1):56-65. PubMed PMID: 1548190.