Estriol | CAS# 50-27-1 (free base) | estrogen medication

MedKoo Cat#: 315241 | Name: Estriol

Description:

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

Estriol is an estrogen, specifically an agonist of the estrogen receptors ERα and ERβ. It is a far less potent estrogen than is estradiol, and as such is a relatively weak estrogen. According to one in vitro study, the relative binding affinity (RBA) of estriol for the human ERα and ERβ was 11.3% and 17.6% of that estradiol, respectively, and the relative transactivational capacity of estriol at the ERα and ERβ was 10.6% and 16.6% of that of estradiol, respectively. Estriol is used as a medication, primarily in hormone therapy for menopausal symptoms.

Chemical Structure

Estriol

CAS#50-27-1 (free base)

Theoretical Analysis

MedKoo Cat#: 315241

Name: Estriol

CAS#: 50-27-1 (free base)

Chemical Formula: C18H24O3

Exact Mass: 288.1725

Molecular Weight: 288.38

Elemental Analysis: C, 74.97; H, 8.39; O, 16.64

Price and Availability

Size	Price	Availability
250mg	USD 110.00	Ready to ship
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 450.00	Ready to ship
5g	USD 950.00	Ready to ship
10g	USD 1,650.00	Ready to ship

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Related CAS #

514-68-1 (succinate) 50-27-1 (free base)

Synonym

Estriol; Oestriol; Trihydroxyestrin; Aacifemine; NSC-12169; NSC12169; NSC 12169;

IUPAC/Chemical Name

(8R,9S,13S,14S,16R,17R)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol

InChi Key

PROQIPRRNZUXQM-ZXXIGWHRSA-N

InChi Code

InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1

SMILES Code

OC1=CC=C2[C@@]3([H])CC[C@]4(C)[C@@H](O)[C@H](O)C[C@@]4([H])[C@]3([H])CCC2=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

Certificate of Analysis

View CoA: current batch, Lot#A24T07K02

QC Data

View QC data: current batch, Lot#A24T07K02

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Estriol is an antagonist of the G-protein coupled estrogen receptor in estrogen receptor-negative breast cancer cells.

In vitro activity:

Cell number of HCC1806 cells increased at 10-8 M 17β-estradiol to 127 ± 8% of control. In cells pretreated with 10-4 M estriol cell number significantly decreased to 54 ± 7% of control (p < 0.05) despite stimulation with 10-8M 17β-estradiol (Figure 3A). In cell line HCC70 10-8 M 17β-estradiol increased cell number to 116% of control, co-treatment with 10-4 M estriol significantly decreased cell number to 64% of control (p < 0.01) (Figure 3B). Estriol clearly prevented the stimulation of proliferation by 17β-estradiol in both TNBC cell lines. Antiproliferative effects of estriol paralleled the amount of GPR30 expressed in the various cell lines (Figure 1). Reference: BMC Cancer. 2014; 14: 935. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4364648/

In vivo activity:

Furthermore, clinical IAV-associated disease—defined by alterations in breathing, posture, and activity—which was evident at 8 and 11 dpi, was significantly reduced in E3 (estriol)-treated compared with placebo-treated females (Fig. 1c). Because the therapeutic benefit of E3 in ameliorating disease in the EAE mouse model has also been demonstrated in males, this study evaluated the efficacy of E3 treatment of IAV-infected male mice. Similar to the phenotype observed for females, E3 conferred significant protection against clinical disease and body weight loss in males (Fig. 1e and 1f), suggesting that E3 mediates effects independent of biological sex. Reference: Endocrinology. 2018 Sep; 159(9): 3306–3320. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6109301/

	Solvent	mg/mL	mM
Solubility
	DMSO	59.0	204.59
	DMF	30.0	104.03
	DMF:PBS (pH 7.2) (1:1)	0.5	1.73
	Ethanol	7.5	26.01

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 288.38 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. Girgert R, Emons G, Gründker C. Inhibition of GPR30 by estriol prevents growth stimulation of triple-negative breast cancer cells by 17β-estradiol. BMC Cancer. 2014 Dec 11;14:935. doi: 10.1186/1471-2407-14-935. PMID: 25496649; PMCID: PMC4364648. 2. Diller M, Schüler S, Buchholz S, Lattrich C, Treeck O, Ortmann O. Effects of estriol on growth, gene expression and estrogen response element activation in human breast cancer cell lines. Maturitas. 2014 Apr;77(4):336-43. doi: 10.1016/j.maturitas.2014.01.004. Epub 2014 Jan 23. PMID: 24529907. 3. Vermillion MS, Ursin RL, Attreed SE, Klein SL. Estriol Reduces Pulmonary Immune Cell Recruitment and Inflammation to Protect Female Mice From Severe Influenza. Endocrinology. 2018 Sep 1;159(9):3306-3320. doi: 10.1210/en.2018-00486. PMID: 30032246; PMCID: PMC6109301. 4. Yamabe N, Kang KS, Lee W, Kim SN, Zhu BT. Estriol blunts postprandial blood glucose rise in male rats through regulating intestinal glucose transporters. Am J Physiol Endocrinol Metab. 2015 Mar 1;308(5):E370-9. doi: 10.1152/ajpendo.00209.2013. Epub 2014 Dec 16. PMID: 25516546; PMCID: PMC4346740.

In vitro protocol:

In vivo protocol:

1. Vermillion MS, Ursin RL, Attreed SE, Klein SL. Estriol Reduces Pulmonary Immune Cell Recruitment and Inflammation to Protect Female Mice From Severe Influenza. Endocrinology. 2018 Sep 1;159(9):3306-3320. doi: 10.1210/en.2018-00486. PMID: 30032246; PMCID: PMC6109301. 2. Yamabe N, Kang KS, Lee W, Kim SN, Zhu BT. Estriol blunts postprandial blood glucose rise in male rats through regulating intestinal glucose transporters. Am J Physiol Endocrinol Metab. 2015 Mar 1;308(5):E370-9. doi: 10.1152/ajpendo.00209.2013. Epub 2014 Dec 16. PMID: 25516546; PMCID: PMC4346740.

1: Donders G, Bellen G, Neven P, Grob P, Prasauskas V, Buchholz S, Ortmann O. Effect of ultra-low-dose estriol and lactobacilli vaginal tablets (Gynoflor®) on inflammatory and infectious markers of the vaginal ecosystem in postmenopausal women with breast cancer on aromatase inhibitors. Eur J Clin Microbiol Infect Dis. 2015 Jul 30. [Epub ahead of print] PubMed PMID: 26223323. 2: Caruso S, Cianci S, Amore FF, Ventura B, Bambili E, Spadola S, Cianci A. Quality of life and sexual function of naturally postmenopausal women on an ultralow-concentration estriol vaginal gel. Menopause. 2015 Jun 15. [Epub ahead of print] PubMed PMID: 26079974. 3: Castellani D, Saldutto P, Galica V, Pace G, Biferi D, Paradiso Galatioto G, Vicentini C. Low-Dose Intravaginal Estriol and Pelvic Floor Rehabilitation in Post-Menopausal Stress Urinary Incontinence. Urol Int. 2015 May 30. [Epub ahead of print] PubMed PMID: 26043913. 4: Soghra K, Zohreh S, Kobra AK, Reza MM. Single measurement of salivary estriol as a predictor of preterm birth. Pak J Biol Sci. 2014 May;17(5):730-4. PubMed PMID: 26031009. 5: Tomi M, Eguchi H, Ozaki M, Tawara T, Nishimura S, Higuchi K, Maruyama T, Nishimura T, Nakashima E. Role of OAT4 in Uptake of Estriol Precursor 16α-Hydroxydehydroepiandrosterone Sulfate Into Human Placental Syncytiotrophoblasts From Fetus. Endocrinology. 2015 Jul;156(7):2704-12. doi: 10.1210/en.2015-1130. Epub 2015 Apr 28. PubMed PMID: 25919187. 6: Durković J, Milenković T, Krone N, Parajes S, Mandić B. Low estriol levels in the maternal marker screen as a predictor of X-linked adrenal hypoplasia congenita: case report. Srp Arh Celok Lek. 2014 Nov-Dec;142(11-12):728-31. PubMed PMID: 25731006. 7: Liu ZH, Lu GN, Yin H, Dang Z. Do we underestimate the concentration of estriol in raw municipal wastewater? Environ Sci Pollut Res Int. 2015 Mar;22(6):4753-8. doi: 10.1007/s11356-014-3981-6. Epub 2014 Dec 24. PubMed PMID: 25537286. 8: Shirshev SV, Maslennikova IL, Nekrasova IV. [Effect of Escherichia coli secreted metabolites on functional activity of human neutrophils against the background of estriol effect]. Zh Mikrobiol Epidemiol Immunobiol. 2014 Sep-Oct;(5):65-70. Russian. PubMed PMID: 25536774. 9: Yamabe N, Kang KS, Lee W, Kim SN, Zhu BT. Estriol blunts postprandial blood glucose rise in male rats through regulating intestinal glucose transporters. Am J Physiol Endocrinol Metab. 2015 Mar 1;308(5):E370-9. doi: 10.1152/ajpendo.00209.2013. Epub 2014 Dec 16. PubMed PMID: 25516546; PubMed Central PMCID: PMC4346740. 10: Girgert R, Emons G, Gründker C. Inhibition of GPR30 by estriol prevents growth stimulation of triple-negative breast cancer cells by 17β-estradiol. BMC Cancer. 2014 Dec 11;14:935. doi: 10.1186/1471-2407-14-935. PubMed PMID: 25496649; PubMed Central PMCID: PMC4364648.