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MedKoo Cat#: 461811 | Name: Sarcophytol A

Description:

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

Sarcophytol A is a cembrane-type diterpene isolated from the marine soft coral Sarcophyton glaucum that has anticancer effects.

Chemical Structure

Sarcophytol A
Sarcophytol A
CAS#72629-69-7

Theoretical Analysis

MedKoo Cat#: 461811

Name: Sarcophytol A

CAS#: 72629-69-7

Chemical Formula: C20H32O

Exact Mass: 288.2453

Molecular Weight: 288.47

Elemental Analysis: C, 83.27; H, 11.18; O, 5.55

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
Sarcophytol A; Sarcophytol-A;
IUPAC/Chemical Name
(S,2Z,4E,8E,12E)-2-isopropyl-5,9,13-trimethylcyclotetradeca-2,4,8,12-tetraen-1-ol
InChi Key
YADVRLOQIWILGX-MIWLTHJTSA-N
InChi Code
InChI=1S/C20H32O/c1-15(2)19-13-12-17(4)10-6-8-16(3)9-7-11-18(5)14-20(19)21/h8,11-13,15,20-21H,6-7,9-10,14H2,1-5H3/b16-8+,17-12+,18-11+,19-13-/t20-/m0/s1
SMILES Code
O[C@@H]1/C(C(C)C)=C\C=C(C)\CC/C=C(C)/CC/C=C(C)/C1
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 288.47 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: Yokomatsu H, Satake K, Hiura A, Tsutsumi M, Suganuma M. Sarcophytol A: a new chemotherapeutic and chemopreventive agent for pancreatic cancer. Pancreas. 1994 Jul;9(4):526-30. PubMed PMID: 7937700. 2: Yamauchi O, Omori M, Ninomiya M, Okuno M, Moriwaki H, Suganuma M, Fujiki H, Muto Y. Inhibitory effect of sarcophytol A on development of spontaneous hepatomas in mice. Jpn J Cancer Res. 1991 Nov;82(11):1234-8. PubMed PMID: 1684357; PubMed Central PMCID: PMC5918333. 3: Wei H, Frenkel K. Suppression of tumor promoter-induced oxidative events and DNA damage in vivo by sarcophytol A: a possible mechanism of antipromotion. Cancer Res. 1992 Apr 15;52(8):2298-303. PubMed PMID: 1559232. 4: Koh M, Iwanaga T, Hatanaka M, Nakano A, Morihara K, Takemura K. Distribution of sarcophytol A in soft coral of the Sarcophyton genus. Biosci Biotechnol Biochem. 2000 Apr;64(4):858-61. PubMed PMID: 10830506. 5: Kobayashi M, Kobayashi K, Nomura M, Munakata H. Conformational study of the cembranoid sarcophytol A, a potent anti-tumor-promoter. Chem Pharm Bull (Tokyo). 1990 Mar;38(3):815-7. PubMed PMID: 2347029. 6: Kobayashi M, Kondo K, Osabe K, Mitsuhashi H. Marine terpenes and terpenoids. V. Oxidation of sarcophytol A, a potent anti-tumor-promoter from the soft coral Sarcophyton glaucum. Chem Pharm Bull (Tokyo). 1988 Jul;36(7):2331-41. PubMed PMID: 2907304. 7: Yokomatsu H, Hiura A, Tsutsumi M, Satake K. Inhibitory effect of sarcophytol A on pancreatic carcinogenesis after initiation by N-nitrosobis(2-oxypropyl)amine in Syrian hamsters. Pancreas. 1996 Aug;13(2):154-9. PubMed PMID: 8829183. 8: Weitberg AB, Corvese D. The effect of epigallocatechin galleate and sarcophytol A on DNA strand breakage induced by tobacco-specific nitrosamines and stimulated human phagocytes. J Exp Clin Cancer Res. 1999 Sep;18(3):433-7. PubMed PMID: 10606191. 9: Narisawa T, Takahashi M, Niwa M, Fukaura Y, Fujiki H. Inhibition of methylnitrosourea-induced large bowel cancer development in rats by sarcophytol A, a product from a marine soft coral Sarcophyton glaucum. Cancer Res. 1989 Jun 15;49(12):3287-9. PubMed PMID: 2720682. 10: Nakagane T, Ishitani R. Presence of specific binding sites for [3H]sarcophytol-A in cultured human skin fibroblasts. Experientia. 1990 May 15;46(5):490-2. PubMed PMID: 2347400. 11: Fujiki H, Suganuma M, Suguri H, Yoshizawa S, Takagi K, Kobayashi M. Sarcophytols A and B inhibit tumor promotion by teleocidin in two-stage carcinogenesis in mouse skin. J Cancer Res Clin Oncol. 1989;115(1):25-8. PubMed PMID: 2493457. 12: Komori A, Suganuma M, Okabe S, Zou X, Tius MA, Fujiki H. Canventol inhibits tumor promotion in CD-1 mouse skin through inhibition of tumor necrosis factor alpha release and of protein isoprenylation. Cancer Res. 1993 Aug 1;53(15):3462-4. PubMed PMID: 8339247. 13: Fujiki H, Suganuma M, Komori A, Yatsunami J, Okabe S, Ohta T, Sueoka E. A new tumor promotion pathway and its inhibitors. Cancer Detect Prev. 1994;18(1):1-7. Review. PubMed PMID: 8162603. 14: Ye JJ, Frenkel K, Zadunaisky JA. Lens opacification and H2O2 elevation induced by a tumor promoter. Lens Eye Toxic Res. 1992;9(1):37-48. PubMed PMID: 1599906. 15: Suganuma M, Okabe S, Sueoka E, Iida N, Komori A, Kim SJ, Fujiki H. A new process of cancer prevention mediated through inhibition of tumor necrosis factor alpha expression. Cancer Res. 1996 Aug 15;56(16):3711-5. PubMed PMID: 8706012. 16: Janairo JR, Janairo GC, Ragasa CY, Bowden BF. A marine verticillane diterpenoid from Cespitularia erecta. Nat Prod Res. 2008 Jan 10;22(1):48-52. PubMed PMID: 17999338. 17: 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. 18: 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. 19: Fujiki H. [Chemoprevention of cancer]. Gan To Kagaku Ryoho. 1986 Dec;13(12):3384-91. Japanese. PubMed PMID: 3789751. 20: Muto Y, Ninomiya M, Fujiki H. Present status of research on cancer chemoprevention in Japan. Jpn J Clin Oncol. 1990 Sep;20(3):219-24. Review. PubMed PMID: 2255099.