Allylpyrocatechol

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

MedKoo CAT#: 526389

CAS#: 1125-74-2

Description: Allylpyrocatechol is an antioxidant, attenuating collagen-induced arthritis via attenuation of oxidative stress secondary to modulation of the MAPK, JAK/STAT, and Nrf2/HO-1 pathways.

Chemical Structure

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Allylpyrocatechol
CAS# 1125-74-2
Instruction

Theoretical Analysis

MedKoo Cat#: 526389
Name: Allylpyrocatechol
CAS#: 1125-74-2
Chemical Formula: C9H10O2
Exact Mass: 150.07
Molecular Weight: 150.177
Elemental Analysis: C, 71.98; H, 6.71; O, 21.31

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Allylpyrocatechol

IUPAC/Chemical Name: 3-Prop-2-enylbenzene-1,2-diol

InChi Key: PARWTEYYJSDGQM-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H10O2/c1-2-4-7-5-3-6-8(10)9(7)11/h2-3,5-6,10-11H,1,4H2

SMILES Code: OC1=CC=CC(CC=C)=C1O

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 150.18 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:
In vitro protocol:
In vivo protocol:

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1: De S, Manna A, Kundu S, De Sarkar S, Chatterjee U, Sen T, Chattopadhyay S, Chatterjee M. Allylpyrocatechol Attenuates Collagen-Induced Arthritis via Attenuation of Oxidative Stress Secondary to Modulation of the MAPK, JAK/STAT, and Nrf2/HO-1 Pathways. J Pharmacol Exp Ther. 2017 Feb;360(2):249-259. doi: 10.1124/jpet.116.238444. Epub 2016 Nov 17. PubMed PMID: 27856937.

2: Hussain RM, Abdullah NF, Amom Z. Killing of Staphylococcus aureus by allylpyrocatechol is potentiated by induction of intracellular oxidative stress and inhibition of catalase activity. J Integr Med. 2016 Nov;14(6):456-464. doi: 10.1016/S2095-4964(16)60279-0. PubMed PMID: 27854197.

3: Haslan H, Suhaimi FH, Thent ZC, Das S. The underlying mechanism of action for various medicinal properties of Piper betle (betel). Clin Ter. 2015;166(5):208-14. doi: 10.7417/CT.2015.1880. Review. PubMed PMID: 26550811.

4: Sujarwo W, Keim AP, Savo V, Guarrera PM, Caneva G. Ethnobotanical study of Loloh: Traditional herbal drinks from Bali (Indonesia). J Ethnopharmacol. 2015 Jul 1;169:34-48. doi: 10.1016/j.jep.2015.03.079. Epub 2015 Apr 8. PubMed PMID: 25861955.

5: Fazal F, Mane PP, Rai MP, Thilakchand KR, Bhat HP, Kamble PS, Palatty PL, Baliga MS. The phytochemistry, traditional uses and pharmacology of Piper Betel. linn (Betel Leaf): A pan-asiatic medicinal plant. Chin J Integr Med. 2014 Aug 26. [Epub ahead of print] PubMed PMID: 25159859.

6: Lei HP, Chen XQ, Qiao CF, Liu Y, Zhao J. [Chemical constituents from twigs of Piper hancei]. Zhong Yao Cai. 2014 Jan;37(1):69-71. Chinese. PubMed PMID: 25090708.

7: Iyer MK, Nayak R, Colah R, Chattopadhyay S. Attenuation of oxidative hemolysis of human red blood cells by the natural phenolic compound, allylpyrocatechol. Free Radic Res. 2013 Sep;47(9):710-7. doi: 10.3109/10715762.2013.816847. Epub 2013 Jul 16. PubMed PMID: 23822150.

8: Yadav SK, Adhikary B, Bandyopadhyay SK, Chattopadhyay S. Inhibition of TNF-α, and NF-κB and JNK pathways accounts for the prophylactic action of the natural phenolic, allylpyrocatechol against indomethacin gastropathy. Biochim Biophys Acta. 2013 Jun;1830(6):3776-86. doi: 10.1016/j.bbagen.2013.03.013. Epub 2013 Mar 21. PubMed PMID: 23523691.

9: Sarkar D, Kundu S, De S, Hariharan C, Saha P, Manna A, Chattopadhyay S, Chatterjee M. The antioxidant activity of allylpyrocatechol is mediated via decreased generation of free radicals along with escalation of antioxidant mechanisms. Phytother Res. 2013 Mar;27(3):324-9. doi: 10.1002/ptr.4720. Epub 2012 May 14. PubMed PMID: 22585425.

10: Kundu S, Bala A, Ghosh P, Mukhopadhyay D, Mitra A, Sarkar A, Bauri AK, Ghosh A, Chattopadhyay S, Chatterjee M. Attenuation of oxidative stress by allylpyrocatechol in synovial cellular infiltrate of patients with Rheumatoid Arthritis. Free Radic Res. 2011 May;45(5):518-26. doi: 10.3109/10715762.2011.555480. Epub 2011 Feb 1. PubMed PMID: 21284489.

11: Yadav SK, Adhikary B, Maity B, Bandyopadhyay SK, Chattopadhyay S. The gastric ulcer-healing action of allylpyrocatechol is mediated by modulation of arginase metabolism and shift of cytokine balance. Eur J Pharmacol. 2009 Jul 1;614(1-3):106-13. doi: 10.1016/j.ejphar.2009.04.046. Epub 2009 May 3. PubMed PMID: 19409889.

12: Sarkar D, Saha P, Gamre S, Bhattacharjee S, Hariharan C, Ganguly S, Sen R, Mandal G, Chattopadhyay S, Majumdar S, Chatterjee M. Anti-inflammatory effect of allylpyrocatechol in LPS-induced macrophages is mediated by suppression of iNOS and COX-2 via the NF-kappaB pathway. Int Immunopharmacol. 2008 Sep;8(9):1264-71. doi: 10.1016/j.intimp.2008.05.003. Epub 2008 Jun 6. PubMed PMID: 18602073.

13: Banerjee D, Bhattacharya S, Bandyopadhyay SK, Chattopadhyay S. Biochemical mechanism of healing activity of the natural phenolic, allylpyrocatechol against indomethacin-induced gastric ulceration in mice. Dig Dis Sci. 2008 Nov;53(11):2868-77. doi: 10.1007/s10620-008-0266-2. Epub 2008 Apr 23. PubMed PMID: 18431645.

14: Mula S, Banerjee D, Patro BS, Bhattacharya S, Barik A, Bandyopadhyay SK, Chattopadhyay S. Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages. Bioorg Med Chem. 2008 Mar 15;16(6):2932-8. doi: 10.1016/j.bmc.2007.12.052. Epub 2007 Dec 31. PubMed PMID: 18207412.

15: Bhattacharya S, Banerjee D, Bauri AK, Chattopadhyay S, Bandyopadhyay SK. Healing property of the Piper betel phenol, allylpyrocatechol against indomethacin-induced stomach ulceration and mechanism of action. World J Gastroenterol. 2007 Jul 21;13(27):3705-13. PubMed PMID: 17659730; PubMed Central PMCID: PMC4250642.

16: Rathee JS, Patro BS, Mula S, Gamre S, Chattopadhyay S. Antioxidant activity of piper betel leaf extract and its constituents. J Agric Food Chem. 2006 Nov 29;54(24):9046-54. PubMed PMID: 17117789.

17: Ramji N, Ramji N, Iyer R, Chandrasekaran S. Phenolic antibacterials from Piper betle in the prevention of halitosis. J Ethnopharmacol. 2002 Nov;83(1-2):149-52. PubMed PMID: 12413722.