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MedKoo Cat#: 540245 | Name: Kahweol
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Description:

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

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.

Chemical Structure

Kahweol
Kahweol
CAS#6894-43-5

Theoretical Analysis

MedKoo Cat#: 540245

Name: Kahweol

CAS#: 6894-43-5

Chemical Formula: C20H26O3

Exact Mass: 314.1882

Molecular Weight: 314.43

Elemental Analysis: C, 76.40; H, 8.34; O, 15.27

Price and Availability

Size Price Availability Quantity
5mg USD 285.00 2 Weeks
10mg USD 450.00 2 Weeks
25mg USD 950.00 2 Weeks
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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
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).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Kahweol is one of the consituents of the coffee from Coffea Arabica with anti-inflammatory anti-angiogenic, and anti-cancerous activities.
In vitro activity:
This study found that kahweol induces apoptosis by inhibiting phosphorylation of Src, and also inhibiting p-mTOR and p-STAT3. Therefore, this study suggests that kahweol is a potent inhibitor of HCC cell growth. Reference: Int J Mol Sci. 2021 Sep 29;22(19):10509. https://pubmed.ncbi.nlm.nih.gov/34638852/
In vivo activity:
Administration of kahweol reduced serum levels of liver injury indicators and ameliorated histological abnormalities in APAP-treated mice. Kahweol inhibited lipid peroxidation and nucleic acid oxidation with restoration of glutathione content and stimulation of nuclear factor erythroid-2-related factor 2-dependent cellular defense system. Reference: Biomed Res Int. 2022 Feb 27;2022:8121124. https://pubmed.ncbi.nlm.nih.gov/35265717/
Solvent mg/mL mM
Solubility
DMF 5.0 0.64
DMSO 18.2 57.77
Ethanol 5.0 0.64
Ethanol:PBS (pH 7.2) (1:5) 0.0 0.06
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 314.43 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
Formulation protocol:
1. Seo HY, Lee SH, Lee JH, Lee JH, Jang BK, Kim MK. Kahweol Induces Apoptosis in Hepatocellular Carcinoma Cells by Inhibiting the Src/mTOR/STAT3 Signaling Pathway. Int J Mol Sci. 2021 Sep 29;22(19):10509. doi: 10.3390/ijms221910509. PMID: 34638852; PMCID: PMC8508869. 2. El-Huneidi W, Anjum S, Bajbouj K, Abu-Gharbieh E, Taneera J. The Coffee Diterpene, Kahweol, Ameliorates Pancreatic β-Cell Function in Streptozotocin (STZ)-Treated Rat INS-1 Cells through NF-kB and p-AKT/Bcl-2 Pathways. Molecules. 2021 Aug 26;26(17):5167. doi: 10.3390/molecules26175167. PMID: 34500601; PMCID: PMC8434527. 3. Kim JY, Leem J, Kim GM. Kahweol Protects against Acetaminophen-Induced Hepatotoxicity in Mice through Inhibiting Oxidative Stress, Hepatocyte Death, and Inflammation. Biomed Res Int. 2022 Feb 27;2022:8121124. doi: 10.1155/2022/8121124. PMID: 35265717; PMCID: PMC8898811. 4. Guzzo LS, Oliveira CC, Ferreira RCM, Machado DPD, Castor MGM, Perez AC, Piscitelli F, Marzo VD, Romero TRL, Duarte IDG. Kahweol, a natural diterpene from coffee, induces peripheral antinociception by endocannabinoid system activation. Braz J Med Biol Res. 2021 Oct 29;54(12):e11071. doi: 10.1590/1414-431X2021e11071. PMID: 34730678; PMCID: PMC8555452.
In vitro protocol:
1. Seo HY, Lee SH, Lee JH, Lee JH, Jang BK, Kim MK. Kahweol Induces Apoptosis in Hepatocellular Carcinoma Cells by Inhibiting the Src/mTOR/STAT3 Signaling Pathway. Int J Mol Sci. 2021 Sep 29;22(19):10509. doi: 10.3390/ijms221910509. PMID: 34638852; PMCID: PMC8508869. 2. El-Huneidi W, Anjum S, Bajbouj K, Abu-Gharbieh E, Taneera J. The Coffee Diterpene, Kahweol, Ameliorates Pancreatic β-Cell Function in Streptozotocin (STZ)-Treated Rat INS-1 Cells through NF-kB and p-AKT/Bcl-2 Pathways. Molecules. 2021 Aug 26;26(17):5167. doi: 10.3390/molecules26175167. PMID: 34500601; PMCID: PMC8434527.
In vivo protocol:
1. Kim JY, Leem J, Kim GM. Kahweol Protects against Acetaminophen-Induced Hepatotoxicity in Mice through Inhibiting Oxidative Stress, Hepatocyte Death, and Inflammation. Biomed Res Int. 2022 Feb 27;2022:8121124. doi: 10.1155/2022/8121124. PMID: 35265717; PMCID: PMC8898811. 2. Guzzo LS, Oliveira CC, Ferreira RCM, Machado DPD, Castor MGM, Perez AC, Piscitelli F, Marzo VD, Romero TRL, Duarte IDG. Kahweol, a natural diterpene from coffee, induces peripheral antinociception by endocannabinoid system activation. Braz J Med Biol Res. 2021 Oct 29;54(12):e11071. doi: 10.1590/1414-431X2021e11071. PMID: 34730678; PMCID: PMC8555452.
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.

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