Cafestol | CAS# 469-83-0 | Diterpene Molecule

MedKoo Cat#: 564298 | Name: Cafestol

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Description:

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

Cafestol is a natural bioactive substance in coffee, having antidiabetic properties in KKAy mice. Cafestol has been shown to exercise anti-angiogenic and anti-tumorigenic effects.

Chemical Structure

Cafestol

CAS#469-83-0

Theoretical Analysis

MedKoo Cat#: 564298

Name: Cafestol

CAS#: 469-83-0

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
10mg	USD 350.00	2 Weeks
50mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

Cafestol

IUPAC/Chemical Name

(3bS,5aS,7R,8R,10aR,10bS)-7-(Hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol

InChi Key

DNJVYWXIDISQRD-HWUKTEKMSA-N

InChi Code

InChI=1S/C20H28O3/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/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1

SMILES Code

O[C@]([C@]1([H])CC2)(CO)C[C@](CC[C@@]34[H])(C1)[C@]2([H])[C@]3(C)CCC5=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

>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

Instruction

View handling instruction

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.

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: van Dam RM, Hu FB, Willett WC. Coffee, Caffeine, and Health. N Engl J Med. 2020 Jul 23;383(4):369-378. doi: 10.1056/NEJMra1816604. PMID: 32706535. 2: Ren Y, Wang C, Xu J, Wang S. Cafestol and Kahweol: A Review on Their Bioactivities and Pharmacological Properties. Int J Mol Sci. 2019 Aug 30;20(17):4238. doi: 10.3390/ijms20174238. PMID: 31480213; PMCID: PMC6747192. 3: Eldesouki S, Qadri R, Abu Helwa R, Barqawi H, Bustanji Y, Abu-Gharbieh E, El- Huneidi W. Recent Updates on the Functional Impact of Kahweol and Cafestol on Cancer. Molecules. 2022 Oct 28;27(21):7332. doi: 10.3390/molecules27217332. PMID: 36364160; PMCID: PMC9654648. 4: Butt MS, Sultan MT. Coffee and its consumption: benefits and risks. Crit Rev Food Sci Nutr. 2011 Apr;51(4):363-73. doi: 10.1080/10408390903586412. PMID: 21432699. 5: Surma S, Oparil S. Coffee and Arterial Hypertension. Curr Hypertens Rep. 2021 Aug 9;23(7):38. doi: 10.1007/s11906-021-01156-3. PMID: 34370111; PMCID: PMC8352830. 6: Gökcen BB, Şanlier N. Coffee consumption and disease correlations. Crit Rev Food Sci Nutr. 2019;59(2):336-348. doi: 10.1080/10408398.2017.1369391. Epub 2017 Sep 29. PMID: 28853910. 7: Liao XL, Chen XZ, Yu KB, Li GY. 16-O-Methyl-cafestol. Acta Crystallogr Sect E Struct Rep Online. 2010 Mar 6;66(Pt 4):o760. doi: 10.1107/S1600536810007920. PMID: 21580605; PMCID: PMC2983991. 8: Liu JC, Chen PY, Hao WR, Liu YC, Lyu PC, Hong HJ. Cafestol Inhibits High- Glucose-Induced Cardiac Fibrosis in Cardiac Fibroblasts and Type 1-Like Diabetic Rats. Evid Based Complement Alternat Med. 2020 Dec 31;2020:4503747. doi: 10.1155/2020/4503747. PMID: 33488743; PMCID: PMC7790572. 9: Socała K, Szopa A, Serefko A, Poleszak E, Wlaź P. Neuroprotective Effects of Coffee Bioactive Compounds: A Review. Int J Mol Sci. 2020 Dec 24;22(1):107. doi: 10.3390/ijms22010107. PMID: 33374338; PMCID: PMC7795778. 10: Farias-Pereira R, Kim E, Park Y. Cafestol increases fat oxidation and energy expenditure in Caenorhabditis elegans via DAF-12-dependent pathway. Food Chem. 2020 Mar 1;307:125537. doi: 10.1016/j.foodchem.2019.125537. Epub 2019 Oct 1. PMID: 31644978. 11: Ji J, Wu L, Feng J, Mo W, Wu J, Yu Q, Li S, Zhang J, Dai W, Xu X, Mao Y, Xu S, Chen K, Li J, Guo C. Cafestol preconditioning attenuates apoptosis and autophagy during hepatic ischemia-reperfusion injury by inhibiting ERK/PPARγ pathway. Int Immunopharmacol. 2020 Jul;84:106529. doi: 10.1016/j.intimp.2020.106529. Epub 2020 Apr 27. PMID: 32344356. 12: Ludwig IA, Clifford MN, Lean ME, Ashihara H, Crozier A. Coffee: biochemistry and potential impact on health. Food Funct. 2014 Aug;5(8):1695-717. doi: 10.1039/c4fo00042k. PMID: 24671262. 13: Hao WR, Sung LC, Chen CC, Hong HJ, Liu JC, Chen JJ. Cafestol Activates Nuclear Factor Erythroid-2 Related Factor 2 and Inhibits Urotensin II-Induced Cardiomyocyte Hypertrophy. Am J Chin Med. 2019;47(2):337-350. doi: 10.1142/S0192415X19500162. Epub 2019 Mar 14. PMID: 30871360. 14: Hoang MH, Nguyen TAT, Nguyen VNH, Vo TN. Cafestol analogues from Coffea canephora: in vitro inhibition and molecular docking to α-glucosidase. Nat Prod Res. 2022 Sep 12:1-7. doi: 10.1080/14786419.2022.2123479. Epub ahead of print. PMID: 36094050. 15: Tsai YT, Sung LC, Haw WR, Chen CC, Huang SF, Liu JC, Cheng TH, Chen PY, Loh SH, Tsai CS. Cafestol, a coffee diterpene, inhibits urotensin II-induced interleukin-8 expression in human umbilical vein endothelial cells. Eur J Pharmacol. 2018 Feb 5;820:106-112. doi: 10.1016/j.ejphar.2017.12.030. Epub 2017 Dec 12. PMID: 29246853. 16: Lima CS, Spindola DG, Bechara A, Garcia DM, Palmeira-Dos-Santos C, Peixoto- da-Silva J, Erustes AG, Michelin LFG, Pereira GJS, Smaili SS, Paredes-Gamero E, Calgarotto AK, Oliveira CR, Bincoletto C. Cafestol, a diterpene molecule found in coffee, induces leukemia cell death. Biomed Pharmacother. 2017 Aug;92:1045-1054. doi: 10.1016/j.biopha.2017.05.109. Epub 2017 Jun 10. PMID: 28618649. 17: Cavin C, Holzhaeuser D, Scharf G, Constable A, Huber WW, Schilter B. Cafestol and kahweol, two coffee specific diterpenes with anticarcinogenic activity. Food Chem Toxicol. 2002 Aug;40(8):1155-63. doi: 10.1016/s0278-6915(02)00029-7. PMID: 12067578. 18: Mellbye FB, Jeppesen PB, Shokouh P, Laustsen C, Hermansen K, Gregersen S. Cafestol, a Bioactive Substance in Coffee, Has Antidiabetic Properties in KKAy Mice. J Nat Prod. 2017 Aug 25;80(8):2353-2359. doi: 10.1021/acs.jnatprod.7b00395. Epub 2017 Aug 1. PMID: 28763212. 19: Rustan AC, Halvorsen B, Ranheim T, Drevon CA. Cafestol (a coffee lipid) decreases uptake of low-density lipoprotein (LDL) in human skin fibroblasts and liver cells. Ann N Y Acad Sci. 1997 Sep 20;827:158-62. doi: 10.1111/j.1749-6632.1997.tb51830.x. PMID: 9329750. 20: Rendón MY, Dos Santos Scholz MB, Bragagnolo N. Is cafestol retained on the paper filter in the preparation of filter coffee? Food Res Int. 2017 Oct;100(Pt 1):798-803. doi: 10.1016/j.foodres.2017.08.013. Epub 2017 Aug 5. PMID: 28873752.