MedKoo Cat#: 597307 | Name: Zaragozic acid B

Description:

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

Zaragozic acid B is a fungal metabolite.

Chemical Structure

Zaragozic acid B
Zaragozic acid B
CAS#146389-61-9

Theoretical Analysis

MedKoo Cat#: 597307

Name: Zaragozic acid B

CAS#: 146389-61-9

Chemical Formula: C39H54O13

Exact Mass: 730.3564

Molecular Weight: 730.84

Elemental Analysis: C, 64.09; H, 7.45; O, 28.46

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 #
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Synonym
Zaragozic acid B;
IUPAC/Chemical Name
(1S,3S,4S,5R,6R,7R)-4,7-dihydroxy-1-((E)-4-hydroxy-3,5-dimethyl-8-phenyloct-7-en-1-yl)-6-(((6E,12E)-tetradeca-6,12-dienoyl)oxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
InChi Key
VFZAKIFLDMCTJV-NZHUAJKLSA-N
InChi Code
InChI=1S/C39H54O13/c1-4-5-6-7-8-9-10-11-12-13-17-23-29(40)50-32-31(42)37(51-33(34(43)44)38(49,35(45)46)39(32,52-37)36(47)48)25-24-27(3)30(41)26(2)19-18-22-28-20-15-14-16-21-28/h4-5,10-11,14-16,18,20-22,26-27,30-33,41-42,49H,6-9,12-13,17,19,23-25H2,1-3H3,(H,43,44)(H,45,46)(H,47,48)/b5-4+,11-10+,22-18+/t26?,27?,30?,31-,32-,33-,37+,38-,39+/m1/s1
SMILES Code
C/C=C/CCCC/C=C/CCCCC(O[C@@H]1[C@H]([C@]2(O[C@@H]([C@@](C(O)=O)([C@]1(C(O)=O)O2)O)C(O)=O)CCC(C(C(C/C=C/c3ccccc3)C)O)C)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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 730.84 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: Suzuki T, Suzuki ST, Yamada I, Koashi Y, Yamada K, Chida N. Total synthesis of spicamycin. J Org Chem. 2002 May 3;67(9):2874-80. PubMed PMID: 11975540. 2: Sakai T, Kawai H, Kamishohara M, Odagawa A, Suzuki A, Uchida T, Kawasaki T, Tsuruo T, Otake N. Structure-antitumor activity relationship of semi-synthetic Spicamycin derivatives. J Antibiot (Tokyo). 1995 Dec;48(12):1467-80. PubMed PMID: 8557605. 3: Sakai T, Kawai H, Kamishohara M, Odagawa A, Suzuki A, Uchida T, Kawasaki T, Tsuruo T, Otake N. Synthesis and antitumor activities of glycine-exchanged analogs of spicamycin. J Antibiot (Tokyo). 1995 Jun;48(6):504-8. PubMed PMID: 7622437. 4: Kamishohara M, Kawai H, Odagawa A, Isoe T, Mochizuki J, Uchida T, Hayakawa Y, Seto H, Tsuruo T, Otake N. Antitumor activity of SPM VIII, a derivative of the nucleoside antibiotic spicamycin, against human tumor xenografts. J Antibiot (Tokyo). 1994 Nov;47(11):1305-11. PubMed PMID: 8002395. 1: Hornby JM, Nickerson KW. Enhanced production of farnesol by Candida albicans treated with four azoles. Antimicrob Agents Chemother. 2004 Jun;48(6):2305-7. PubMed PMID: 15155241; PubMed Central PMCID: PMC415631. 2: Hornby JM, Kebaara BW, Nickerson KW. Farnesol biosynthesis in Candida albicans: cellular response to sterol inhibition by zaragozic acid B. Antimicrob Agents Chemother. 2003 Jul;47(7):2366-9. PubMed PMID: 12821501; PubMed Central PMCID: PMC161837. 3: Alaei P, MacNulty EE, Ryder NS. Inhibition of protein prenylation down-regulates signalling by inflammatory mediators in human keratinocytes. Biochem Biophys Res Commun. 1996 May 6;222(1):133-8. PubMed PMID: 8630058. 4: Bergstrom JD, Dufresne C, Bills GF, Nallin-Omstead M, Byrne K. Discovery, biosynthesis, and mechanism of action of the zaragozic acids: potent inhibitors of squalene synthase. Annu Rev Microbiol. 1995;49:607-39. Review. PubMed PMID: 8561474. 5: Bansal VS, Vaidya S. Characterization of two distinct allyl pyrophosphatase activities from rat liver microsomes. Arch Biochem Biophys. 1994 Dec;315(2):393-9. PubMed PMID: 7986083. 6: Bergstrom JD, Kurtz MM, Rew DJ, Amend AM, Karkas JD, Bostedor RG, Bansal VS, Dufresne C, VanMiddlesworth FL, Hensens OD, et al. Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase. Proc Natl Acad Sci U S A. 1993 Jan 1;90(1):80-4. PubMed PMID: 8419946; PubMed Central PMCID: PMC45603. 5: Kamishohara M, Kawai H, Odagawa A, Isoe T, Mochizuki J, Uchida T, Hayakawa Y, Seto H, Tsuruo T, Otake N. Structure-antitumor activity relationship of semi-synthetic spicamycin analogues. J Antibiot (Tokyo). 1993 Sep;46(9):1439-46. PubMed PMID: 8226322.