Pogostone | CAS#23800-56-8 | antifungal

MedKoo Cat#: 585047 | Name: Pogostone

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Description:

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

Pogostone is a pyranone that has been found in the essential oil of P. cablin, also known as patchouli oil, and has antifungal and insecticidal activities.

Chemical Structure

Pogostone

CAS#23800-56-8

Theoretical Analysis

MedKoo Cat#: 585047

Name: Pogostone

CAS#: 23800-56-8

Chemical Formula: C12H16O4

Exact Mass: 224.1049

Molecular Weight: 224.26

Elemental Analysis: C, 64.27; H, 7.19; O, 28.54

Price and Availability

Size	Price	Availability
10mg	USD 285.00	2 Weeks
25mg	USD 550.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Pogostone; Dhelwangin;

IUPAC/Chemical Name

4-hydroxy-6-methyl-3-(4-methyl-1-oxopentyl)-2H-pyran-2-one

InChi Key

AJFJTORMMHWKFW-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H16O4/c1-7(2)4-5-9(13)11-10(14)6-8(3)16-12(11)15/h6-7,14H,4-5H2,1-3H3

SMILES Code

O=C1C(C(CCC(C)C)=O)=C(O)C=C(C)O1

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

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Pogostone is isolated from patchouli oil with anti-bacterial and anti-cancer activities. Pogostone inhibits both gram negative and gram positive bacteria, also show inhibitory effect on corynebacterium xerosis with a MIC value of 0.098 µg/ml.

In vitro activity:

This study observed the effects of pogostone (PO) on osteoclast differentiation, bone resorption function and other indicators, and F-actin ring formation by using Trap staining, SEM and immunofluorescence, and further explored the targets of pogostone in regulating osteoclast differentiation and function using qPCR and Western Blot. Pogostone inhibits osteoclast differentiation, bone resorption, formation of F-actin ring, and the expression of specific genes by attenuated NF-kB degradation and phosphorylation of JNK. In vitro, pogostone suppresses invasion of breast cancer cells, migration, and promotes their apoptosis. Reference: Life Sci. 2023 Apr 15:121611. https://pubmed.ncbi.nlm.nih.gov/37068706/

In vivo activity:

In vivo, the anti-tumor effect of pogostone was tested with HCT116 colorectal tumor cells transplantation tumor model. In vivo, 150mg/kg pogostone inhibited the HCT116 tumor growth in immunodeficient mice with an inhibitory rate of 43.3%, decreased the expression of Ki67, and induced apoptosis in three days. Reference: J Ethnopharmacol. 2017 Apr 18;202:20-27. https://pubmed.ncbi.nlm.nih.gov/27416805/

	Solvent	mg/mL	mM
Solubility
	DMF	1.6	7.13
	DMSO	51.5	229.65
	Ethanol	3.0	13.38
	Ethanol:PBS (pH 7.2) (1:5)	0.2	0.71

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 224.26 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. Zheng T, Lin Z, Jiang G, Chen H, Zeng X, Yang Y. Pogostone attenuates osteolysis in breast cancer by inhibiting the NF-kB and JNK signaling pathways of osteoclast. Life Sci. 2023 Apr 15:121611. doi: 10.1016/j.lfs.2023.121611. Epub ahead of print. PMID: 37068706. 2. Li D, Xing Z, Yu T, Dong W, Wang Z, Peng C, Yang C. Pogostone attenuates adipose tissue inflammation by regulating the adipocyte-macrophage crosstalk via activating SIRT1. Food Funct. 2022 Nov 14;13(22):11853-11864. doi: 10.1039/d2fo01450e. PMID: 36314728. 3. Cao ZX, Yang YT, Yu S, Li YZ, Wang WW, Huang J, Xie XF, Xiong L, Lei S, Peng C. Pogostone induces autophagy and apoptosis involving PI3K/Akt/mTOR axis in human colorectal carcinoma HCT116 cells. J Ethnopharmacol. 2017 Apr 18;202:20-27. doi: 10.1016/j.jep.2016.07.028. Epub 2016 Jul 11. PMID: 27416805. 4. Peng F, Wan F, Xiong L, Peng C, Dai M, Chen J. In vitro and in vivo antibacterial activity of Pogostone. Chin Med J (Engl). 2014;127(23):4001-5. PMID: 25430439.

In vitro protocol:

In vivo protocol:

1. Cao ZX, Yang YT, Yu S, Li YZ, Wang WW, Huang J, Xie XF, Xiong L, Lei S, Peng C. Pogostone induces autophagy and apoptosis involving PI3K/Akt/mTOR axis in human colorectal carcinoma HCT116 cells. J Ethnopharmacol. 2017 Apr 18;202:20-27. doi: 10.1016/j.jep.2016.07.028. Epub 2016 Jul 11. PMID: 27416805. 2. Peng F, Wan F, Xiong L, Peng C, Dai M, Chen J. In vitro and in vivo antibacterial activity of Pogostone. Chin Med J (Engl). 2014;127(23):4001-5. PMID: 25430439.

1: Huang Y, Zhao P, Zhang X, Fu H, Fu C. Uncovering the pharmacological mechanisms of Patchouli essential oil for treating ulcerative colitis. J Ethnopharmacol. 2024 Aug 23:118737. doi: 10.1016/j.jep.2024.118737. Epub ahead of print. PMID: 39182705. 2: Wei CC, Tseng ZR, Liao HW. Discovery and determination of misuse and chemotypes of Pogostemon cablin by liquid chromatography-quadrupole time-of- flight mass spectrometry and liquid chromatography with diode-array detector. J Sep Sci. 2024 Jun;47(12):e2400208. doi: 10.1002/jssc.202400208. PMID: 39031742. 3: Meng X, Zhong Y, Kuang X, Zhang Y, Yang L, Cai Y, Wang F, He F, Xie H, Wang B, Li J. Targeting the STAT3/IL-36G signaling pathway can be a promising approach to treat rosacea. J Adv Res. 2024 Jun 22:S2090-1232(24)00250-9. doi: 10.1016/j.jare.2024.06.013. Epub ahead of print. PMID: 38909883. 4: Zhu Y, Ouyang H, Lv Z, Yao G, Ge M, Cao X, Chang Y, He J. Simultaneous determination of multiple components in rat plasma by UPLC-MS/MS for pharmacokinetic studies after oral administration of Pogostemon cablin extract. Front Pharmacol. 2024 May 22;15:1293464. doi: 10.3389/fphar.2024.1293464. PMID: 38841366; PMCID: PMC11150675. 5: Li H, Zhao L, Liang Z, Wang Z, Hu C, Wang Y, Shen G, Wang S. Identification of Xuanfei Baidu granule constituents by liquid chromatography-quadruple-time- of-flight-mass spectrometry and its anti-inflammatory active constituents using a lipopolysaccharide-induced RAW264.7 cell model. Biomed Chromatogr. 2024 Aug;38(8):e5898. doi: 10.1002/bmc.5898. Epub 2024 May 27. PMID: 38802724. 6: Tang S, Huang S, Huang J, Lai X, Guo J, Huang J, Zhong Y. Pogostone attenuated high-fat diet-induced nonalcoholic fatty liver disease in mice through inhibition of NLRP3 inflammasome signaling. Eur J Pharmacol. 2024 May 5;970:176463. doi: 10.1016/j.ejphar.2024.176463. Epub 2024 Mar 9. PMID: 38461909. 7: Wang D, Yuan C, Li Y, Bai S, Feng J, Wang Y, Fang Y, Zhang Z. Chelation of the Optimal Antifungal Pogostone Analogue with Copper(II) to Explore the Dual Antifungal and Antibacterial Agent. J Agric Food Chem. 2024 Feb 28;72(8):3894-3903. doi: 10.1021/acs.jafc.3c07050. Epub 2024 Feb 17. PMID: 38366986. 8: Zhang H, Ou X, Chen W, Zeng Q, Yan Y, He M, Yan H. Comparative physicochemical, hormonal, transcriptomic and proteomic analyses provide new insights into the formation mechanism of two chemotypes of Pogostemon cablin. PLoS One. 2023 Sep 22;18(9):e0290402. doi: 10.1371/journal.pone.0290402. PMID: 37738267; PMCID: PMC10516424. 9: Wang D, Yuan C, Li J, Fang Y, Zhang Z. Synthesis of Pogostone-Inspired Dehydroacetic Acid Derivatives and Their Antifungal Activity against Sclerotinia sclerotiorum (Lib.) de Bary. Chem Biodivers. 2023 Jun;20(6):e202300128. doi: 10.1002/cbdv.202300128. Epub 2023 May 19. PMID: 37148476. 10: Zheng T, Lin Z, Jiang G, Chen H, Yang Y, Zeng X. Pogostone attenuates osteolysis in breast cancer by inhibiting the NF-kB and JNK signaling pathways of osteoclast. Life Sci. 2023 Sep 1;328:121611. doi: 10.1016/j.lfs.2023.121611. Epub 2023 Apr 15. PMID: 37068706. 11: Li D, Xing Z, Yu T, Dong W, Wang Z, Peng C, Yang C. Pogostone attenuates adipose tissue inflammation by regulating the adipocyte-macrophage crosstalk via activating SIRT1. Food Funct. 2022 Nov 14;13(22):11853-11864. doi: 10.1039/d2fo01450e. PMID: 36314728. 12: Zou W, Deng L, Wu H, Liu Z, Lu W, He Y. Untargeted Metabolomics Profiling Reveals Beneficial Changes in Milk of Sows Supplemented with Fermented Compound Chinese Medicine Feed Additive. Animals (Basel). 2022 Oct 21;12(20):2879. doi: 10.3390/ani12202879. PMID: 36290264; PMCID: PMC9597846. 13: Xie S, Li L, Zhan B, Shen X, Deng X, Tan W, Fang T. Pogostone Enhances the Antibacterial Activity of Colistin against MCR-1-Positive Bacteria by Inhibiting the Biological Function of MCR-1. Molecules. 2022 Apr 28;27(9):2819. doi: 10.3390/molecules27092819. PMID: 35566163; PMCID: PMC9102576. 14: Wang C, Wang Y, Chen J, Liu L, Yang M, Li Z, Wang C, Pichersky E, Xu H. Synthesis of 4-methylvaleric acid, a precursor of pogostone, involves a 2-isobutylmalate synthase related to 2-isopropylmalate synthase of leucine biosynthesis. New Phytol. 2022 Aug;235(3):1129-1145. doi: 10.1111/nph.18186. Epub 2022 May 20. PMID: 35485988. 15: Yan W, Cao S, Wu Y, Ye Z, Zhang C, Yao G, Yu J, Yang D, Zhang J. Integrated Analysis of Physiological, mRNA Sequencing, and miRNA Sequencing Data Reveals a Specific Mechanism for the Response to Continuous Cropping Obstacles in Pogostemon cablin Roots. Front Plant Sci. 2022 Apr 1;13:853110. doi: 10.3389/fpls.2022.853110. PMID: 35432413; PMCID: PMC9010791. 16: Xu F, Cai W, Ma T, Zeng H, Kuang X, Chen W, Liu B. Traditional Uses, Phytochemistry, Pharmacology, Quality Control, Industrial Application, Pharmacokinetics and Network Pharmacology of Pogostemon cablin: A Comprehensive Review. Am J Chin Med. 2022;50(3):691-721. doi: 10.1142/S0192415X22500288. Epub 2022 Mar 10. PMID: 35282804. 17: Homayoun M, Sajedi N, Soleimani M. In vitro evaluation of the pogostone effects on the expression of PTEN and DACT1 tumor suppressor genes, cell cycle, and apoptosis in ovarian cancer cell line. Res Pharm Sci. 2022 Jan 15;17(2):164-175. doi: 10.4103/1735-5362.335175. PMID: 35280836; PMCID: PMC8860107. 18: Zhang H, Deng W, Lu C, He M, Yan H. SMRT sequencing of full-length transcriptome and gene expression analysis in two chemical types of Pogostemon cablin (Blanco) Benth. PeerJ. 2022 Feb 22;10:e12940. doi: 10.7717/peerj.12940. PMID: 35223208; PMCID: PMC8877398. 19: Leong W, Huang G, Liao W, Xia W, Li X, Su Z, Liu L, Wu Q, Wong VKW, Law BYK, Xia C, Guo X, Khan I, Wendy Hsiao WL. Traditional Patchouli essential oil modulates the host's immune responses and gut microbiota and exhibits potent anti-cancer effects in ApcMin /+ mice. Pharmacol Res. 2022 Feb;176:106082. doi: 10.1016/j.phrs.2022.106082. Epub 2022 Jan 13. PMID: 35032662. 20: Yao YY, He ML, Li YY, Xia JH, Yan HJ, Zhang HY. [Biosynthesis and metabolism regulation of terpenoids in Pogostemon cablin: a review]. Zhongguo Zhong Yao Za Zhi. 2021 Nov;46(21):5560-5567. Chinese. doi: 10.19540/j.cnki.cjcmm.20210722.102. PMID: 34951207.