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MedKoo Cat#: 461368 | Name: Restricticin

Description:

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

Restricticin is a naturally-occurring antifungal agent which contains triene, pyran and glycine ester functionalities.

Chemical Structure

Restricticin
Restricticin
CAS#135357-96-9

Theoretical Analysis

MedKoo Cat#: 461368

Name: Restricticin

CAS#: 135357-96-9

Chemical Formula: C19H31NO4

Exact Mass: 337.2253

Molecular Weight: 337.46

Elemental Analysis: C, 67.63; H, 9.26; N, 4.15; O, 18.96

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.
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Related CAS #
No Data
Synonym
Restricticin; Ro 09-1470; Ro-09-1470; Ro09-1470;
IUPAC/Chemical Name
(2R,3S,4R,5R)-2-((2E,4E,6E)-deca-2,4,6-trien-2-yl)-4-methoxy-5-methyltetrahydro-2H-pyran-3-yl glycinate
InChi Key
FIFAQBUMNRZWOQ-OVBFOOSGSA-N
InChi Code
InChI=1S/C19H31NO4/c1-5-6-7-8-9-10-11-14(2)18-19(24-16(21)12-20)17(22-4)15(3)13-23-18/h7-11,15,17-19H,5-6,12-13,20H2,1-4H3/b8-7+,10-9+,14-11+/t15-,17-,18-,19+/m1/s1
SMILES Code
NCC(O[C@@H]1[C@@H](/C(C)=C/C=C/C=C/CCC)OC[C@@H](C)[C@H]1OC)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 337.46 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.

Recalculate based on batch purity %
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: Schwartz RE, Dufresne C, Flor JE, Kempf AJ, Wilson KE, Lam T, Onishi J, Milligan J, Fromtling RA, Abruzzo GK, et al. Restricticin, a novel glycine-containing antifungal agent. J Antibiot (Tokyo). 1991 May;44(5):463-71. PubMed PMID: 2061189. 2: VanMiddlesworth F, Milligan J, Bartizal K, Dufresne C, Onishi J, Abruzzo G, Patchett A, Wilson K. Carbazate as a glycine bioisostere in restricticin. J Antibiot (Tokyo). 1996 Mar;49(3):329-31. PubMed PMID: 8626254. 3: Tsukuda T, Watanabe M, Ontsuka H, Hattori K, Shirai M, Shimma N. Synthesis of novel antifungal agents (2). Bioorg Med Chem Lett. 1998 Jul 21;8(14):1825-8. PubMed PMID: 9873441. 4: Tsukuda T, Shiratori Y, Watanabe M, Ontsuka H, Hattori K, Shirai M, Shimma N. Modeling, synthesis and biological activity of novel antifungal agents (1). Bioorg Med Chem Lett. 1998 Jul 21;8(14):1819-24. PubMed PMID: 9873440. 5: Barrett AG, Bennett AJ, Menzer S, Smith ML, White AJ, Williams DJ. Applications of Crotonyldiisopinocampheylboranes in Synthesis: Total Synthesis of Restrictinol. J Org Chem. 1999 Jan 8;64(1):162-171. PubMed PMID: 11674099. 6: Aoki Y, Yoshihara F, Kondoh M, Nakamura Y, Nakayama N, Arisawa M. Ro 09-1470 is a selective inhibitor of P-450 lanosterol C-14 demethylase of fungi. Antimicrob Agents Chemother. 1993 Dec;37(12):2662-7. PubMed PMID: 8109933; PubMed Central PMCID: PMC192771. 7: Aoki Y, Yamazaki T, Kondoh M, Sudoh Y, Nakayama N, Sekine Y, Shimada H, Arisawa M. A new series of natural antifungals that inhibit P450 lanosterol C-14 demethylase. II. Mode of action. J Antibiot (Tokyo). 1992 Feb;45(2):160-70. PubMed PMID: 1556007. 8: Matsukuma S, Ohtsuka T, Kotaki H, Shirai H, Sano T, Watanabe K, Nakayama N, Itezono Y, Fujiu M, Shimma N, et al. A new series of natural antifungals that inhibit P450 lanosterol C-14 demethylase. I. Taxonomy, fermentation, isolation and structural elucidation. J Antibiot (Tokyo). 1992 Feb;45(2):151-9. PubMed PMID: 1556006.