Zaragozic acid B

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MedKoo CAT#: 597307

CAS#: 146389-61-9

Description: Zaragozic acid B is a fungal metabolite.


Price and Availability

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Pricing updated 2020-08-12. Prices are subject to change without notice.

Zaragozic acid B is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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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


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


Technical Data

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


References

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.