Sarcophine
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MedKoo CAT#: 461808

CAS#: 55038-27-2

Description: Sarcophine is a natural cembranoid from the Red Sea soft coral Sarcophyton glaucum.


Chemical Structure

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Sarcophine
CAS# 55038-27-2

Theoretical Analysis

MedKoo Cat#: 461808
Name: Sarcophine
CAS#: 55038-27-2
Chemical Formula: C20H28O3
Exact Mass: 316.2038
Molecular Weight: 316.44
Elemental Analysis: C, 75.91; H, 8.92; O, 15.17

Price and Availability

Size Price Availability Quantity
5.0mg USD 430.0 2 Weeks
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Synonym: Sarcophine; Sarcophin A; Sarcophin;

IUPAC/Chemical Name: (4Z,11E)-1a,5,8,12-tetramethyl-2,3,6,7,10a,13,14,14a-octahydrooxireno[2',3':9,10]cyclotetradeca[1,2-b]furan-9(1aH)-one

InChi Key: CGAKBBMRMLAYMY-ATYDYJLJSA-N

InChi Code: InChI=1S/C20H28O3/c1-13-6-5-11-20(4)18(23-20)10-8-14(2)12-17-16(9-7-13)15(3)19(21)22-17/h6,12,17-18H,5,7-11H2,1-4H3/b13-6-,14-12+

SMILES Code: O=C1C(C)=C(CC/C(C)=C\CCC(O2)(C)C2CC/C(C)=C/3)C3O1

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

Preparing Stock Solutions

The following data is based on the product molecular weight 316.44 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

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1: Szymanski PT, Ahmed SA, Radwan MM, Khalifa SI, Fahmy H. Evaluation of the anti-melanoma activities of sarcophine, (+)-7alpha,8beta-dihydroxydeepoxysarcophine and sarcophytolide from the Red Sea soft coral Sarcophyton glaucum. Nat Prod Commun. 2014 Feb;9(2):151-4. PubMed PMID: 24689276.

2: Szymanski PT, Ahmed SA, Khalifa S, Tokuda H, Ichiishi E, Iida A, Suzuki N, Fahmy H. Chemopreventive effect of sarcophine-diol on NOR-1-induced TPA-promoted skin carcinogenesis in female HOS:HR-1 mice. Nat Prod Commun. 2013 Feb;8(2):153-4. PubMed PMID: 23513714.

3: Hassan HM, Sallam AA, Mohammed R, Hifnawy MS, Youssef DT, El Sayed KA. Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors. Bioorg Med Chem. 2011 Aug 15;19(16):4928-34. doi: 10.1016/j.bmc.2011.06.060. Epub 2011 Jun 28. PubMed PMID: 21775154.

4: Szymanski PT, Kuppast B, Ahmed SA, Khalifa S, Fahmy H. Sarcophine-diol, a skin cancer chemopreventive agent, inhibits proliferation and stimulates apoptosis in mouse melanoma B₁₆F₁₀ cell line. Mar Drugs. 2012 Jan;10(1):1-19. doi: 10.3390/md10010001. Epub 2011 Dec 22. PubMed PMID: 22363217; PubMed Central PMCID: PMC3280529.

5: Szymanski PT, Muley P, Ahmed SA, Khalifa S, Fahmy H. Sarcophine-diol inhibits expression of COX-2, inhibits activity of cPLA2, enhances degradation of PLA2 and PLC(γ)1 and inhibits cell membrane permeability in mouse melanoma B16F10 cells. Mar Drugs. 2012 Oct;10(10):2166-80. doi: 10.3390/md10102166. Epub 2012 Sep 28. PubMed PMID: 23170076; PubMed Central PMCID: PMC3497015.

6: Sawant SS, Sylvester PW, Avery MA, Desai P, Youssef DT, El Sayed KA. Bioactive rearranged and halogenated semisynthetic derivatives of the marine natural product sarcophine. J Nat Prod. 2004 Dec;67(12):2017-23. PubMed PMID: 15620244.

7: Guillermo RF, Zhang X, Kaushik RS, Zeman D, Ahmed SA, Khalifa S, Fahmy H, Dwivedi C. Dose-response on the chemopreventive effects of sarcophine-diol on UVB-induced skin tumor development in SKH-1 hairless mice. Mar Drugs. 2012 Sep;10(9):2111-25. doi: 10.3390/md10092111. Epub 2012 Sep 24. PubMed PMID: 23118725; PubMed Central PMCID: PMC3475277.

8: Zhang X, Bommareddy A, Chen W, Hildreth MB, Kaushik RS, Zeman D, Khalifa S, Fahmy H, Dwivedi C. Chemopreventive effects of sarcophine-diol on ultraviolet B-induced skin tumor development in SKH-1 hairless mice. Mar Drugs. 2009 Apr 30;7(2):153-65. doi: 10.3390/md7020153. PubMed PMID: 19597578; PubMed Central PMCID: PMC2707040.

9: Sawant S, Youssef D, Mayer A, Sylvester P, Wali V, Arant M, El Sayed K. Anticancer and anti-inflammatory sulfur-containing semisynthetic derivatives of sarcophine. Chem Pharm Bull (Tokyo). 2006 Aug;54(8):1119-23. PubMed PMID: 16880655.

10: Sawant SS, Youssef DT, Reiland J, Ferniz M, Marchetti D, El Sayed KA. Biocatalytic and antimetastatic studies of the marine cembranoids sarcophine and 2-epi-16-deoxysarcophine. J Nat Prod. 2006 Jul;69(7):1010-3. PubMed PMID: 16872134.

11: Zhang X, Kundoor V, Khalifa S, Zeman D, Fahmy H, Dwivedi C. Chemopreventive effects of sarcophine-diol on skin tumor development in CD-1 mice. Cancer Lett. 2007 Aug 8;253(1):53-9. Epub 2007 Feb 23. PubMed PMID: 17321042.

12: Bilasy Sel-S, Khalifa SI, Saleh SM, Abou El-Ela SH. HPLC method for the quantitative determination of sarcophine, a source of cembranoids with cancer chemopreventive activity. J Pharm Biomed Anal. 2008 Mar 13;46(4):784-7. doi: 10.1016/j.jpba.2007.11.030. Epub 2007 Nov 26. PubMed PMID: 18178355.

13: Zhang X, Bommareddy A, Chen W, Khalifa S, Kaushik RS, Fahmy H, Dwivedi C. Sarcophine-diol, a Chemopreventive Agent of Skin Cancer, Inhibits Cell Growth and Induces Apoptosis through Extrinsic Pathway in Human Epidermoid Carcinoma A431 Cells. Transl Oncol. 2009 Mar;2(1):21-30. PubMed PMID: 19252748; PubMed Central PMCID: PMC2647699.

14: Fahmy H, Zjawiony JK, Khalifa S, Fronczek FR. A semi-synthetic analog of the cembranoid sarcophine. Acta Crystallogr C. 2003 Feb;59(Pt 2):o85-7. Epub 2003 Jan 31. PubMed PMID: 12574663.

15: Katsuyama I, Fahmy H, Zjawiony JK, Khalifa SI, Kilada RW, Konoshima T, Takasaki M, Tokuda H. Semisynthesis of new sarcophine derivatives with chemopreventive activity. J Nat Prod. 2002 Dec;65(12):1809-14. PubMed PMID: 12502319.

16: Elkhateeb A, El-Beih AA, Gamal-Eldeen AM, Alhammady MA, Ohta S, Paré PW, Hegazy ME. New terpenes from the Egyptian soft coral Sarcophyton ehrenbergi. Mar Drugs. 2014 Apr 2;12(4):1977-86. doi: 10.3390/md12041977. PubMed PMID: 24699113; PubMed Central PMCID: PMC4012453.

17: Ne'eman I, Fishelson L, Kashman Y. Sarcophine--a new toxin from the soft coral Sarcophyton glaucum (Alcyonaria). Toxicon. 1974 Dec;12(6):593-8. PubMed PMID: 4156432.

18: Erman A, Neéman I. Inhibition of phosphofructokinase by the toxic cembranolide sarcophine isolated from the soft-bodied coral Sarcophyton glaucum. Toxicon. 1977;15(3):207-15. PubMed PMID: 17178.

19: El Sayed KA, Hamann MT, Waddling CA, Jensen C, Lee SK, Dunstan CA, Pezzuto JM. Structurally Novel Bioconversion Products of the Marine Natural Product Sarcophine Effectively Inhibit JB6 Cell Transformation. J Org Chem. 1998 Oct 16;63(21):7449-7455. PubMed PMID: 11672397.

20: Cheng SY, Wang SK, Chiou SF, Hsu CH, Dai CF, Chiang MY, Duh CY. Cembranoids from the octocoral Sarcophyton ehrenbergi. J Nat Prod. 2010 Feb 26;73(2):197-203. doi: 10.1021/np900693r. PubMed PMID: 20099902.