Kahweol Acetate | CAS#81760-47-6 | includes inhibition of RANKL-induced osteoclast generation

MedKoo Cat#: 540247 | Name: Kahweol Acetate

Description:

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

Kahweol Acetate is a semi-synthetic derivative of kahweol, a natural product found 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 Acetate

CAS#81760-47-6 (acetate)

Theoretical Analysis

MedKoo Cat#: 540247

Name: Kahweol Acetate

CAS#: 81760-47-6 (acetate)

Chemical Formula: C22H28O4

Exact Mass: 356.1988

Molecular Weight: 356.46

Elemental Analysis: C, 74.13; H, 7.92; O, 17.95

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Related CAS #

81760-47-6 (acetate) 6894-43-5 (free)

Synonym

Kahweol acetate; CCRIS 1520; CCRIS1520; CCRIS-1520

IUPAC/Chemical Name

((3bS,5aR,7R,8S,10aR,10bS)-7-hydroxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b-decahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-yl)methyl acetate

InChi Key

OJLWVPDNBQAHRT-RWKVYSHYSA-N

InChi Code

InChI=1S/C22H28O4/c1-14(23)26-13-22(24)12-21-9-5-17-16-7-10-25-18(16)6-8-20(17,2)19(21)4-3-15(22)11-21/h6-8,10,15,17,19,24H,3-5,9,11-13H2,1-2H3/t15-,17+,19-,20+,21+,22-/m0/s1

SMILES Code

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

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

Certificate of Analysis

View CoA: current batch, Lot#SCB80910

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Kahweol Acetate is a semi-synthetic derivative of kahweol, a natural product found in coffee beans.

In vitro activity:

This study therefore investigated the effects of kahweol acetate and cafestol on human renal cancer ACHN and Caki-1 cells. Accordingly, the combination of kahweol acetate and cafestol administration synergistically inhibited cell proliferation and migration by inducing apoptosis and inhibiting epithelial-mesenchymal transition. Mechanistic dissection revealed that kahweol acetate and cafestol inhibited Akt and ERK phosphorylation. Reference: Sci Rep. 2021 Jan 12;11(1):675. https://pubmed.ncbi.nlm.nih.gov/33436830/

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
	Soluble in DMSO	0.0	100.00

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 356.46 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

Formulation protocol:

1. Makino T, Izumi K, Hiratsuka K, Kano H, Shimada T, Nakano T, Kadomoto S, Naito R, Iwamoto H, Yaegashi H, Shigehara K, Kadono Y, Nakata H, Saito Y, Nakagawa-Goto K, Sakai N, Iwata Y, Wada T, Mizokami A. Anti-proliferative and anti-migratory properties of coffee diterpenes kahweol acetate and cafestol in human renal cancer cells. Sci Rep. 2021 Jan 12;11(1):675. doi: 10.1038/s41598-020-80302-4. PMID: 33436830; PMCID: PMC7804192. 2. Choi JH, Hwang YP, Jin SW, Lee GH, Kim HG, Han EH, Kim SK, Kang KW, Chung YC, Jeong HG. Suppression of PMA-induced human fibrosarcoma HT-1080 invasion and metastasis by kahweol via inhibiting Akt/JNK1/2/p38 MAPK signal pathway and NF-κB dependent transcriptional activities. Food Chem Toxicol. 2019 Mar;125:1-9. doi: 10.1016/j.fct.2018.12.038. Epub 2018 Dec 24. PMID: 30590137. 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:

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: Lam LK, Yee C, Chung A, Wattenberg LW. Use of silver nitrate impregnated silica cartridges in the separation of kahweol and cafestol esters by preparative liquid chromatography. J Chromatogr. 1985 Jun 28;328:422-4. PubMed PMID: 2993334.