6-Paradol | CAS# 27113-22-0 | Phenolic Ketone

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

MedKoo CAT#: 326793

CAS#: 27113-22-0

Description: Paradol, also known as 6-Paradol, is the active flavor constituent of the seeds of Guinea pepper (Aframomum melegueta or grains of paradise). It is also found in ginger. Paradol has been found to have antioxidant and antitumor promoting effects in a mouse model. It is used in flavors as an essential oil to give spiciness.

Chemical Structure

Paradol

CAS# 27113-22-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326793
Name: Paradol
CAS#: 27113-22-0
Chemical Formula: C17H26O3
Exact Mass: 278.19
Molecular Weight: 278.392
Elemental Analysis: C, 73.35; H, 9.41; O, 17.24

Price and Availability

Size	Price	Availability
200mg	USD 450	2 Weeks
500mg	USD 950	2 Weeks
1g	USD 1650	2 Weeks
2g	USD 2950	2 Weeks
5g	USD 6650	2 Weeks
10g	USD 9950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 6-Paradol; Paradol

IUPAC/Chemical Name: 1-(4-Hydroxy-3-methoxyphenyl)decan-5-one

InChi Key: IKCUWBHTOKPRNS-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H26O3/c1-3-4-5-9-15(18)10-7-6-8-14-11-12-16(19)17(13-14)20-2/h11-13,19H,3-10H2,1-2H3

SMILES Code: CCCCCC(CCCCC1=CC=C(O)C(OC)=C1)=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

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Product Data:

Product Data

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Biological target:	Paradol is an effective inhibitor of tumor promotion in mouse skin carcinogenesis, binds to cyclooxygenase (COX)-2 active site.
In vitro activity:	To further validate whether 6-P had the inhibitory effect on migration and invasion of MIA PaCa-2 and SW1990, transwell assay and wound healing assay were performed to evaluate to migrate and invasive ability. The migration and invasion significantly decreased in the concentration of 40 and 80 μM compared with 0 μM, revealing that 6-P could also partly suppress the metastasis of pancreatic cancer cells. In addition, the epithelial-mesenchymal transition (EMT) was tested using western blot assay to detect the protein levels of E-cadherin, N-cadherin and Vimentin. The results demonstrated that the expression of E-cadherin gradually rose with the increasing concentration of 6-P. Conversely, the expression of N-cadherin and Vimentin gradually reduced with the increasing concentration of 6-P. The results suggested an inhibited function of 6-P on EMT of pancreatic cancer cells. Reference: Cancer Cell Int. 2021 Aug 10;21(1):420. https://pubmed.ncbi.nlm.nih.gov/34376189/
In vivo activity:	The current study evaluates the effect of 6-paradol in amelioration of ulcerative colitis in rats for the first time. Rats were divided randomly into six groups (n = 8). Group one was administered normal saline; group two was treated with the vehicle only; group three, sulfasalazine 500 mg/kg; and groups four, five, and six, were given 6-paradol (50, 100, 200, respectively) mg/kg orally through gastric gavage for 7 days. Colitis was induced on 4th day by intrarectal administration of 2 ml acetic acid (3%), approximately 3 cm from anal verge. Colonic and serum glutathione (GSH) levels decreased, while colonic and serum malondialdehyde (MDA), colonic myeloperoxidase (MPO) activity, serum interleukin-6 (IL-6), serum tumour necrosis factor-α (TNF-α) levels, and colon weight to length ratio were increased significantly in the colitis untreated group compared to normal control. Treatment with 6-paradol considerably improved all these parameters, especially at a dose of 200 mg/kg (p < 0.001), revealing non-significant differences with sulfasalazine 500 mg/kg and normal control (p = 0.998). Sulfasalazine and 6-paradol in a dose dependent manner also markedly reversed mucosal oedema, atrophy and inflammation, cryptic damage, haemorrhage, and ulceration. In conclusion, 6-Paradol demonstrated protection against acetic acid-induced ulcerative colitis, probably by anti-inflammatory and antioxidant actions. Reference: BMC Complement Med Ther. 2021 Jan 13;21(1):28. https://pubmed.ncbi.nlm.nih.gov/33441125/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	82.5	296.34

Preparing Stock Solutions

The following data is based on the product molecular weight 278.39 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. Wang R, Liu T, Chen J, Zhang D. Paradol Induces Cell Cycle Arrest and Apoptosis in Glioblastoma Cells. Nutr Cancer. 2022 Jan 18:1-8. doi: 10.1080/01635581.2022.2028866. Epub ahead of print. PMID: 35040364. 2. Jiang X, Wang J, Chen P, He Z, Xu J, Chen Y, Liu X, Jiang J. [6]-Paradol suppresses proliferation and metastases of pancreatic cancer by decreasing EGFR and inactivating PI3K/AKT signaling. Cancer Cell Int. 2021 Aug 10;21(1):420. doi: 10.1186/s12935-021-02118-0. PMID: 34376189; PMCID: PMC8353760. 3. Rafeeq M, Murad HAS, Abdallah HM, El-Halawany AM. Protective effect of 6-paradol in acetic acid-induced ulcerative colitis in rats. BMC Complement Med Ther. 2021 Jan 13;21(1):28. doi: 10.1186/s12906-021-03203-7. Erratum in: BMC Complement Med Ther. 2021 Feb 10;21(1):60. PMID: 33441125; PMCID: PMC7805070. 4. El-Maadawy WH, Hassan M, Abdou RM, El-Dine RS, Aboushousha T, El-Tanbouly ND, El-Sayed AM. 6-Paradol alleviates Diclofenac-induced acute kidney injury via autophagy enhancement-mediated by AMPK/AKT/mTOR and NLRP3 inflammasome pathways. Environ Toxicol Pharmacol. 2022 Jan 25;91:103817. doi: 10.1016/j.etap.2022.103817. Epub ahead of print. PMID: 35091105.
In vitro protocol:	1. Wang R, Liu T, Chen J, Zhang D. Paradol Induces Cell Cycle Arrest and Apoptosis in Glioblastoma Cells. Nutr Cancer. 2022 Jan 18:1-8. doi: 10.1080/01635581.2022.2028866. Epub ahead of print. PMID: 35040364. 2. Jiang X, Wang J, Chen P, He Z, Xu J, Chen Y, Liu X, Jiang J. [6]-Paradol suppresses proliferation and metastases of pancreatic cancer by decreasing EGFR and inactivating PI3K/AKT signaling. Cancer Cell Int. 2021 Aug 10;21(1):420. doi: 10.1186/s12935-021-02118-0. PMID: 34376189; PMCID: PMC8353760.
In vivo protocol:	1. Rafeeq M, Murad HAS, Abdallah HM, El-Halawany AM. Protective effect of 6-paradol in acetic acid-induced ulcerative colitis in rats. BMC Complement Med Ther. 2021 Jan 13;21(1):28. doi: 10.1186/s12906-021-03203-7. Erratum in: BMC Complement Med Ther. 2021 Feb 10;21(1):60. PMID: 33441125; PMCID: PMC7805070. 2. El-Maadawy WH, Hassan M, Abdou RM, El-Dine RS, Aboushousha T, El-Tanbouly ND, El-Sayed AM. 6-Paradol alleviates Diclofenac-induced acute kidney injury via autophagy enhancement-mediated by AMPK/AKT/mTOR and NLRP3 inflammasome pathways. Environ Toxicol Pharmacol. 2022 Jan 25;91:103817. doi: 10.1016/j.etap.2022.103817. Epub ahead of print. PMID: 35091105.

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1: Setoguchi S, Watase D, Nagata-Akaho N, Haratake A, Matsunaga K, Takata J. Pharmacokinetics of Paradol Analogues Orally Administered to Rats. J Agric Food Chem. 2016 Mar 9;64(9):1932-7. doi: 10.1021/acs.jafc.5b05615. Epub 2016 Feb 24. PubMed PMID: 26868188.

2: Gaire BP, Kwon OW, Park SH, Chun KH, Kim SY, Shin DY, Choi JW. Neuroprotective effect of 6-paradol in focal cerebral ischemia involves the attenuation of neuroinflammatory responses in activated microglia. PLoS One. 2015 Mar 19;10(3):e0120203. doi: 10.1371/journal.pone.0120203. eCollection 2015. PubMed PMID: 25789481; PubMed Central PMCID: PMC4366308.

3: Haratake A, Watase D, Setoguchi S, Terada K, Matsunaga K, Takata J. Relationship between the acyl chain length of paradol analogues and their antiobesity activity following oral ingestion. J Agric Food Chem. 2014 Jul 2;62(26):6166-74. doi: 10.1021/jf500873a. Epub 2014 Jun 18. PubMed PMID: 24909840.

4: Mariadoss AV, Kathiresan S, Muthusamy R, Kathiresan S. Protective effects of [6]-paradol on histological lesions and immunohistochemical gene expression in DMBA induced hamster buccal pouch carcinogenesis. Asian Pac J Cancer Prev. 2013;14(5):3123-9. PubMed PMID: 23803090.

5: Suresh K, Manoharan S, Vijayaanand MA, Sugunadevi G. Chemopreventive and antioxidant efficacy of (6)-paradol in 7,12-dimethylbenz(a)anthracene induced hamster buccal pouch carcinogenesis. Pharmacol Rep. 2010 Nov-Dec;62(6):1178-85. PubMed PMID: 21273675.

6: Iwami M, Mahmoud FA, Shiina T, Hirayama H, Shima T, Sugita J, Shimizu Y. Extract of grains of paradise and its active principle 6-paradol trigger thermogenesis of brown adipose tissue in rats. Auton Neurosci. 2011 Apr 26;161(1-2):63-7. doi: 10.1016/j.autneu.2010.11.012. Epub 2010 Dec 23. PubMed PMID: 21185236.

7: Keum YS, Kim J, Lee KH, Park KK, Surh YJ, Lee JM, Lee SS, Yoon JH, Joo SY, Cha IH, Yook JI. Induction of apoptosis and caspase-3 activation by chemopreventive [6]-paradol and structurally related compounds in KB cells. Cancer Lett. 2002 Mar 8;177(1):41-7. PubMed PMID: 11809529.

8: Chung WY, Jung YJ, Surh YJ, Lee SS, Park KK. Antioxidative and antitumor promoting effects of [6]-paradol and its homologs. Mutat Res. 2001 Sep 20;496(1-2):199-206. PubMed PMID: 11551496.

9: Lee E, Surh YJ. Induction of apoptosis in HL-60 cells by pungent vanilloids, [6]-gingerol and [6]-paradol. Cancer Lett. 1998 Dec 25;134(2):163-8. PubMed PMID: 10025876.

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