Farnesiferol C

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

MedKoo CAT#: 561400

CAS#: 512-17-4

Description: Farnesiferol C induces apoptosis via regulation of L11 and c-Myc. Farnesiferol C has combinational potential with anticancer drugs in non-small-cell lung cancers.


Price and Availability

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Farnesiferol C 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#: 561400
Name: Farnesiferol C
CAS#: 512-17-4
Chemical Formula: C24H30O4
Exact Mass: 382.2144
Molecular Weight: 382.5
Elemental Analysis: C, 75.36; H, 7.91; O, 16.73


Synonym: Farnesiferol C; Farnesiferol-C;

IUPAC/Chemical Name: 7-[(E)-3-Methyl-5-[(1R,3R,4S)-2,2,4-trimethyl-7-oxabicyclo[2.2.1]heptan-3-yl]pent-2-enoxy]chromen-2-one

InChi Key: OCHZHKVSLMBEJP-QYQYHAIPSA-N

InChi Code: InChI=1S/C24H30O4/c1-16(5-9-20-23(2,3)21-11-13-24(20,4)28-21)12-14-26-18-8-6-17-7-10-22(25)27-19(17)15-18/h6-8,10,12,15,20-21H,5,9,11,13-14H2,1-4H3/b16-12+/t20-,21-,24+/m1/s1

SMILES Code: O=C1C=CC2=C(O1)C=C(OC/C=C(C)/CC[C@@H]3C(C)(C)[C@@]4([H])CC[C@]3(C)O4)C=C2


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:
>2 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).

Harmonized System Code:
293490


References

1: Aldaghi L, Rad A, Arab A, Kasaian J, Iranshahi M, Sadr AS, Soltani F. In Silico and In Vitro Evaluation of Cytotoxic Activities of Farnesiferol C and Microlobin on MCF-7, HeLa and KYSE Cell Lines. Drug Res (Stuttg). 2016 Oct;66(10):532-538. Epub 2016 Jul 27. PubMed PMID: 27463028.

2: Jung JH, Kim MJ, Lee H, Lee J, Kim J, Lee HJ, Shin EA, Kim YH, Kim B, Shim BS, Kim SH. Farnesiferol c induces apoptosis via regulation of L11 and c-Myc with combinational potential with anticancer drugs in non-small-cell lung cancers. Sci Rep. 2016 May 27;6:26844. doi: 10.1038/srep26844. PubMed PMID: 27231235; PubMed Central PMCID: PMC4882547.

3: Kasaian J, Mosaffa F, Behravan J, Masullo M, Piacente S, Iranshahi M. Modulation of Multidrug Resistance Protein 2 Efflux in the Cisplatin Resistance Human Ovarian Carcinoma Cells A2780/RCIS by Sesquiterpene Coumarins. Phytother Res. 2016 Jan;30(1):84-9. doi: 10.1002/ptr.5504. Epub 2015 Oct 27. PubMed PMID: 26503061.

4: Aas Z, Babaei E, Hosseinpour Feizi MA, Dehghan G. Anti-proliferative and Apoptotic Effects of Dendrosomal Farnesiferol C on Gastric Cancer Cells. Asian Pac J Cancer Prev. 2015;16(13):5325-9. PubMed PMID: 26225673.

5: Kasaian J, Mosaffa F, Behravan J, Masullo M, Piacente S, Ghandadi M, Iranshahi M. Reversal of P-glycoprotein-mediated multidrug resistance in MCF-7/Adr cancer cells by sesquiterpene coumarins. Fitoterapia. 2015 Jun;103:149-54. doi: 10.1016/j.fitote.2015.03.025. Epub 2015 Apr 3. PubMed PMID: 25843566.

6: Dastan D, Salehi P, Reza Gohari A, Ebrahimi SN, Aliahmadi A, Hamburger M. Bioactive sesquiterpene coumarins from Ferula pseudalliacea. Planta Med. 2014 Aug;80(13):1118-23. doi: 10.1055/s-0034-1382996. Epub 2014 Aug 19. PubMed PMID: 25137575.

7: Cha MR, Choi YH, Choi CW, Kim YS, Kim YK, Ryu SY, Kim YH, Choi SU. Galbanic acid, a cytotoxic sesquiterpene from the gum resin of Ferula asafoetida, blocks protein farnesyltransferase. Planta Med. 2011 Jan;77(1):52-4. doi: 10.1055/s-0030-1250049. Epub 2010 Jun 17. PubMed PMID: 20560115.

8: Lee JH, Choi S, Lee Y, Lee HJ, Kim KH, Ahn KS, Bae H, Lee HJ, Lee EO, Ahn KS, Ryu SY, Lü J, Kim SH. Herbal compound farnesiferol C exerts antiangiogenic and antitumor activity and targets multiple aspects of VEGFR1 (Flt1) or VEGFR2 (Flk1) signaling cascades. Mol Cancer Ther. 2010 Feb;9(2):389-99. doi: 10.1158/1535-7163.MCT-09-0775. Epub 2010 Jan 26. PubMed PMID: 20103598.

9: Ghosh A, Banerji A, Mandal S, Banerji J. A new sesquiterpenoid coumarin from Ferula assafoetida. Nat Prod Commun. 2009 Aug;4(8):1023-4. PubMed PMID: 19768976.

10: Yang JR, Jing S, Li ZH, Qin HL. [Chemical constituents from roots of Ferula sinkiangensis]. Zhongguo Zhong Yao Za Zhi. 2007 Nov;32(22):2382-4. Chinese. PubMed PMID: 18257264.

11: Rollinger JM, Steindl TM, Schuster D, Kirchmair J, Anrain K, Ellmerer EP, Langer T, Stuppner H, Wutzler P, Schmidtke M. Structure-based virtual screening for the discovery of natural inhibitors for human rhinovirus coat protein. J Med Chem. 2008 Feb 28;51(4):842-51. doi: 10.1021/jm701494b. Epub 2008 Feb 5. PubMed PMID: 18247552.

12: Iranshahi M, Arfa P, Ramezani M, Jaafari MR, Sadeghian H, Bassarello C, Piacente S, Pizza C. Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial activity of 7-prenyloxycoumarins against promastigotes. Phytochemistry. 2007 Feb;68(4):554-61. Epub 2006 Dec 29. PubMed PMID: 17196626.