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

MedKoo CAT#: 540245

CAS#: 6894-43-5

Description: Kahweol is a natural product in coffee beans. It exhibits a wide variety of biological activities, including inhibiting RANKL-induced osteoclast generation, inducing cell cycle arrest and apoptosis in oral squamous cell carcinoma cells, preventing aflatoxin B1 induced DNA adduct formation, and suppressing H2O2-induced DNA damage and oxidative stress.


Price and Availability

Size
Price

5mg
USD 200
Size
Price

10mg
USD 350
Size
Price

25mg
USD 685

Kahweol purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540245
Name: Kahweol
CAS#: 6894-43-5
Chemical Formula: C20H26O3
Exact Mass: 314.1882
Molecular Weight: 314.42
Elemental Analysis: C, 76.40; H, 8.34; O, 15.27


Related CAS #: 6894-43-5   81760-47-6  

Synonym: CCRIS 1521; CCRIS1521; CCRIS-1521; Kahweol

IUPAC/Chemical Name: (3bS,5aS,7R,8R,10aR,10bS)-7-(hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b-decahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol

InChi Key: JEKMKNDURXDJAD-HWUKTEKMSA-N

InChi Code: InChI=1S/C20H26O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1

SMILES Code: OC[C@@]([C@]1([H])CC2)(O)C[C@](CC[C@@]34[H])(C1)[C@]2([H])[C@]3(C)C=CC5=C4C=CO5


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: Guzzo LS, Romero TR, Queiroz-Junior CM, Caliari MV, Azevedo AO, Perez AC, Duarte ID. Involvement of endogenous opioid peptides in the peripheral antinociceptive effect induced by the coffee specific diterpene kahweol. Pharmacol Rep. 2015 Oct;67(5):1010-5. doi: 10.1016/j.pharep.2015.02.009. Epub 2015 Mar 27. PubMed PMID: 26398397.

2: Chae JI, Jeon YJ, Shim JH. Anti-proliferative properties of kahweol in oral squamous cancer through the regulation specificity protein 1. Phytother Res. 2014 Dec;28(12):1879-86. doi: 10.1002/ptr.5217. Epub 2014 Sep 8. PubMed PMID: 25196544.

3: Choi DW, Lim MS, Lee JW, Chun W, Lee SH, Nam YH, Park JM, Choi DH, Kang CD, Lee SJ, Park SC. The Cytotoxicity of Kahweol in HT-29 Human Colorectal Cancer Cells Is Mediated by Apoptosis and Suppression of Heat Shock Protein 70 Expression. Biomol Ther (Seoul). 2015 Mar;23(2):128-33. doi: 10.4062/biomolther.2014.133. Epub 2015 Mar 1. PubMed PMID: 25767680; PubMed Central PMCID: PMC4354313.

4: Park GH, Song HM, Jeong JB. The coffee diterpene kahweol suppresses the cell proliferation by inducing cyclin D1 proteasomal degradation via ERK1/2, JNK and GKS3β-dependent threonine-286 phosphorylation in human colorectal cancer cells. Food Chem Toxicol. 2016 Sep;95:142-8. doi: 10.1016/j.fct.2016.07.008. Epub 2016 Jul 14. PubMed PMID: 27424123.

5: Jeon YJ, Bang W, Cho JH, Lee RH, Kim SH, Kim MS, Park SM, Shin JC, Chung HJ, Oh KB, Seo JM, Ko S, Shim JH, Chae JI. Kahweol induces apoptosis by suppressing BTF3 expression through the ERK signaling pathway in non-small cell lung cancer cells. Int J Oncol. 2016 Dec;49(6):2294-2302. doi: 10.3892/ijo.2016.3727. Epub 2016 Oct 12. PubMed PMID: 27748804.

6: Cárdenas C, Quesada AR, Medina MÁ. Insights on the antitumor effects of kahweol on human breast cancer: decreased survival and increased production of reactive oxygen species and cytotoxicity. Biochem Biophys Res Commun. 2014 May 9;447(3):452-8. doi: 10.1016/j.bbrc.2014.04.026. Epub 2014 Apr 13. PubMed PMID: 24732357.

7: Guzzo LS, Castor MG, Perez Ade C, Duarte ID, Romero TR. Natural Diterpenes from Coffee, Cafestol, and Kahweol Induce Peripheral Antinoceception by Adrenergic System Interaction. Planta Med. 2016 Jan;82(1-2):106-12. doi: 10.1055/s-0035-1558084. Epub 2015 Oct 13. PubMed PMID: 26460671.

8: Fumimoto R, Sakai E, Yamaguchi Y, Sakamoto H, Fukuma Y, Nishishita K, Okamoto K, Tsukuba T. The coffee diterpene kahweol prevents osteoclastogenesis via impairment of NFATc1 expression and blocking of Erk phosphorylation. J Pharmacol Sci. 2012;118(4):479-86. Epub 2012 Mar 23. PubMed PMID: 22447306.

9: Chartier A, Beaumesnil M, de Oliveira AL, Elfakir C, Bostyn S. Optimization of the isolation and quantitation of kahweol and cafestol in green coffee oil. Talanta. 2013 Dec 15;117:102-11. doi: 10.1016/j.talanta.2013.07.053. Epub 2013 Aug 29. PubMed PMID: 24209317.

10: Fukuma Y, Sakai E, Nishishita K, Okamoto K, Tsukuba T. Cafestol has a weaker inhibitory effect on osteoclastogenesis than kahweol and promotes osteoblast differentiation. Biofactors. 2015 Jul-Aug;41(4):222-31. doi: 10.1002/biof.1218. Epub 2015 Jul 7. PubMed PMID: 26154488.

11: Cárdenas C, Quesada AR, Medina MA. Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene. PLoS One. 2011;6(8):e23407. doi: 10.1371/journal.pone.0023407. Epub 2011 Aug 9. Erratum in: PLoS One. 2011;6(11). doi:10.1371/annotation/38262cc6-07cc-4074-8ce7-2181d4d0fbdc. PubMed PMID: 21858104; PubMed Central PMCID: PMC3153489.

12: Um HJ, Park JW, Kwon TK. Melatonin sensitizes Caki renal cancer cells to kahweol-induced apoptosis through CHOP-mediated up-regulation of PUMA. J Pineal Res. 2011 May;50(4):359-66. doi: 10.1111/j.1600-079X.2010.00851.x. Epub 2011 Jan 18. PubMed PMID: 21244481.

13: Lee KA, Chae JI, Shim JH. Natural diterpenes from coffee, cafestol and kahweol induce apoptosis through regulation of specificity protein 1 expression in human malignant pleural mesothelioma. J Biomed Sci. 2012 Jun 26;19:60. doi: 10.1186/1423-0127-19-60. PubMed PMID: 22734486; PubMed Central PMCID: PMC3431247.

14: Um HJ, Oh JH, Kim YN, Choi YH, Kim SH, Park JW, Kwon TK. The coffee diterpene kahweol sensitizes TRAIL-induced apoptosis in renal carcinoma Caki cells through down-regulation of Bcl-2 and c-FLIP. Chem Biol Interact. 2010 Jun 7;186(1):36-42. doi: 10.1016/j.cbi.2010.04.013. Epub 2010 Apr 18. PubMed PMID: 20403343.

15: Shen T, Park YC, Kim SH, Lee J, Cho JY. Nuclear factor-kappaB/signal transducers and activators of transcription-1-mediated inflammatory responses in lipopolysaccharide-activated macrophages are a major inhibitory target of kahweol, a coffee diterpene. Biol Pharm Bull. 2010;33(7):1159-64. PubMed PMID: 20606307.

16: Moeenfard M, Cortez A, Machado V, Costa R, Luís C, Coelho P, Soares R, Alves A, Borges N, Santos A. Anti-Angiogenic Properties of Cafestol and Kahweol Palmitate Diterpene Esters. J Cell Biochem. 2016 Dec;117(12):2748-2756. doi: 10.1002/jcb.25573. Epub 2016 May 8. PubMed PMID: 27129115.

17: Kim JY, Kim DH, Jeong HG. Inhibitory effect of the coffee diterpene kahweol on carrageenan-induced inflammation in rats. Biofactors. 2006;26(1):17-28. PubMed PMID: 16614480.

18: Kim HG, Hwang YP, Jeong HG. Kahweol blocks STAT3 phosphorylation and induces apoptosis in human lung adenocarcinoma A549 cells. Toxicol Lett. 2009 May 22;187(1):28-34. doi: 10.1016/j.toxlet.2009.01.022. Epub 2009 Jan 24. PubMed PMID: 19429240.

19: Kim JY, Jung KS, Lee KJ, Na HK, Chun HK, Kho YH, Jeong HG. The coffee diterpene kahweol suppress the inducible nitric oxide synthase expression in macrophages. Cancer Lett. 2004 Sep 30;213(2):147-54. PubMed PMID: 15327829.

20: Oh JH, Lee JT, Yang ES, Chang JS, Lee DS, Kim SH, Choi YH, Park JW, Kwon TK. The coffee diterpene kahweol induces apoptosis in human leukemia U937 cells through down-regulation of Akt phosphorylation and activation of JNK. Apoptosis. 2009 Nov;14(11):1378-86. doi: 10.1007/s10495-009-0407-x. PubMed PMID: 19768546.