Propyl pyrazole triol | CAS#263717-53-9 | ERalpha agonist

MedKoo Cat#: 561241 | Name: Propyl pyrazole triol

Description:

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

PPT, also known as Propyl pyrazole triol, is an estrogen receptor (ERalpha) agonist. PPT also exerts anti-diabetic effects in mouse models.

Chemical Structure

Propyl pyrazole triol

CAS#263717-53-9

Theoretical Analysis

MedKoo Cat#: 561241

Name: Propyl pyrazole triol

CAS#: 263717-53-9

Chemical Formula: C24H22N2O3

Exact Mass: 386.1630

Molecular Weight: 386.45

Elemental Analysis: C, 74.59; H, 5.74; N, 7.25; O, 12.42

Price and Availability

Size	Price	Availability
100mg	USD 750.00	2 Weeks
500mg	USD 1,650.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,250.00	2 Weeks

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Related CAS #

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Synonym

PPT; Propyl pyrazole triol

IUPAC/Chemical Name

4-Propyl-1,3,5-tri((4-hydroxy)phenyl)pyrazole

InChi Key

IOTXSIGGFRQYKW-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H22N2O3/c1-2-3-22-23(16-4-10-19(27)11-5-16)25-26(18-8-14-21(29)15-9-18)24(22)17-6-12-20(28)13-7-17/h4-15,27-29H,2-3H2,1H3

SMILES Code

OC1=CC=C(C2=C(CCC)C(C3=CC=C(O)C=C3)=NN2C4=CC=C(O)C=C4)C=C1

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

Instruction

View handling instruction

Biological target:

Propyl pyrazole triol (PPT) is a selective estrogen receptor alpha (ERα) agonist.

In vitro activity:

At 1000 ng/ml of tetracycline, when expression of ERβ is suppressed, PPT was able to induce cell proliferation to a level of 173%, an induction level that was slightly higher than the maximal induction of cell proliferation by E2 (164%) under these conditions. This is in spite of the fact that the affinity of ERα for PPT was lower than for E2. Although the E2-induced proliferation with full expression of ERβ was reached at 3nM of PPT (153%), no considerable reduction of proliferation compared with E2 (124%) was observed under all ERα/ERβ ratios studied due to the inability of PPT to activate ERβ. Reference: Toxicol Sci. 2008 Oct;105(2):303-11. https://pubmed.ncbi.nlm.nih.gov/18644836/

In vivo activity:

In a short-term (4 d) uterotrophic assay, PPT was found to be as efficacious as 17alpha-ethinyl-17beta-estradiol in stimulating uterine weight gain and up-regulating complement 3 gene expression. In a 6-wk chronic model, PPT completely prevented the ovariectomy-induced body weight increase and loss of bone mineral density. It also increased uterine weight and markedly reduced plasma cholesterol levels in these mature animals. PPT was also effective in the brain. It increased progesterone receptor mRNA in the arcuate and ventromedial nuclei of the hypothalamus and prevented experimentally induced hot flushes. Reference: Endocrinology. 2002 Nov;143(11):4172-7. https://pubmed.ncbi.nlm.nih.gov/12399409/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	51.75
	DMSO	58.9	152.44
	DMSO:PBS (pH 7.2) (1:10)	0.2	0.39
	Ethanol	29.6	76.71

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 386.45 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. Jiang M, Liu Z, Shao J, Zhou J, Wang H, Song C, Li X, Wang L, Xu Q, Liu X, Lin L, Zhang R. Estrogen receptor α regulates phenotypic switching and proliferation of vascular smooth muscle cells through the NRF1-OMI-mitophagy signaling pathway under simulated microgravity. Front Physiol. 2022 Nov 10;13:1039913. doi: 10.3389/fphys.2022.1039913. PMID: 36439260; PMCID: PMC9691402. 2. Sotoca AM, van den Berg H, Vervoort J, van der Saag P, Ström A, Gustafsson JA, Rietjens I, Murk AJ. Influence of cellular ERalpha/ERbeta ratio on the ERalpha-agonist induced proliferation of human T47D breast cancer cells. Toxicol Sci. 2008 Oct;105(2):303-11. doi: 10.1093/toxsci/kfn141. Epub 2008 Jul 21. PMID: 18644836; PMCID: PMC2527638. 3. Khaksari M, Hajializadeh Z, Mahani SE, Soltani Z, Asadikaram G. Estrogen receptor agonists induce anti‑edema effects by altering α and β estrogen receptor gene expression. Acta Neurobiol Exp (Wars). 2021;81(3):286-294. doi: 10.21307/ane-2021-027. PMID: 34672299. 4. Harris HA, Katzenellenbogen JA, Katzenellenbogen BS. Characterization of the biological roles of the estrogen receptors, ERalpha and ERbeta, in estrogen target tissues in vivo through the use of an ERalpha-selective ligand. Endocrinology. 2002 Nov;143(11):4172-7. doi: 10.1210/en.2002-220403. PMID: 12399409.

In vitro protocol:

In vivo protocol:

1. Khaksari M, Hajializadeh Z, Mahani SE, Soltani Z, Asadikaram G. Estrogen receptor agonists induce anti‑edema effects by altering α and β estrogen receptor gene expression. Acta Neurobiol Exp (Wars). 2021;81(3):286-294. doi: 10.21307/ane-2021-027. PMID: 34672299. 2. Harris HA, Katzenellenbogen JA, Katzenellenbogen BS. Characterization of the biological roles of the estrogen receptors, ERalpha and ERbeta, in estrogen target tissues in vivo through the use of an ERalpha-selective ligand. Endocrinology. 2002 Nov;143(11):4172-7. doi: 10.1210/en.2002-220403. PMID: 12399409.

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PubMed PMID: 27399230. 13: Tada Y, Makino H, Furukawa H, Shimada K, Wada K, Liang EI, Murakami S, Kudo M, Kung DK, Hasan DM, Kitazato KT, Nagahiro S, Lawton MT, Hashimoto T. Roles of estrogen in the formation of intracranial aneurysms in ovariectomized female mice. Neurosurgery. 2014 Dec;75(6):690-5; discussion 695. doi: 10.1227/NEU.0000000000000528. PubMed PMID: 25181430; PubMed Central PMCID: PMC4399640. 14: Gajewska A, Zielinska-Gorska M, Wasilewska-Dziubinska E, Baran M, Kotarba G, Gorski K. Pituitary galaninergic system activity in female rats: the regulatory role of gonadal steroids. J Physiol Pharmacol. 2016 Jun;67(3):423-9. PubMed PMID: 27512003. 15: Pisani SL, Neese SL, Katzenellenbogen JA, Schantz SL, Korol DL. Estrogen Receptor-Selective Agonists Modulate Learning in Female Rats in a Dose- and Task-Specific Manner. Endocrinology. 2016 Jan;157(1):292-303. doi: 10.1210/en.2015-1616. Epub 2015 Oct 14. PubMed PMID: 26465198; PubMed Central PMCID: PMC4701887. 16: Bishop CV, Xu F, Molskness TA, Stouffer RL, Hennebold JD. Dynamics of Immune Cell Types Within the Macaque Corpus Luteum During the Menstrual Cycle: Role of Progesterone. Biol Reprod. 2015 Nov;93(5):112. doi: 10.1095/biolreprod.115.132753. Epub 2015 Sep 23. PubMed PMID: 26400401; PubMed Central PMCID: PMC5333802. 17: Kurt AH, Bozkus F, Uremis N, Uremis MM. The protective role of G protein-coupled estrogen receptor 1 (GPER-1) on methotrexate-induced nephrotoxicity in human renal epithelium cells. Ren Fail. 2016 Jun;38(5):686-92. doi: 10.3109/0886022X.2016.1155398. Epub 2016 Mar 16. PubMed PMID: 26981789. 18: Smith LC, Ralston-Hooper KJ, Ferguson PL, Sabo-Attwood T. The G Protein-Coupled Estrogen Receptor Agonist G-1 Inhibits Nuclear Estrogen Receptor Activity and Stimulates Novel Phosphoproteomic Signatures. Toxicol Sci. 2016 Jun;151(2):434-46. doi: 10.1093/toxsci/kfw057. Epub 2016 Mar 29. PubMed PMID: 27026707; PubMed Central PMCID: PMC4880142. 19: Gajewska A, Herman AP, Wolińska-Witort E, Kochman K, Zwierzchowski L. In vivo oestrogenic modulation of Egr1 and Pitx1 gene expression in female rat pituitary gland. J Mol Endocrinol. 2014 Dec;53(3):355-66. doi: 10.1530/JME-14-0092. Epub 2014 Sep 25. PubMed PMID: 25258388. 20: Yang F, Tao J, Xu L, Zhao N, Chen J, Chen W, Zhu Y, Qiu J. Estradiol decreases rat depressive behavior by estrogen receptor beta but not alpha: no correlation with plasma corticosterone. Neuroreport. 2014 Jan 22;25(2):100-4. doi: 10.1097/WNR.0000000000000052. PubMed PMID: 24128867.