4-[(2Z,4Z)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol

• ChemBase ID: 767
• Molecular Formular: C18H18O2
• Molecular Mass: 266.33432
• Monoisotopic Mass: 266.13067982
• SMILES: Oc1ccc(C(=CC)C(=CC)c2ccc(O)cc2)cc1
• Canonical SMILES: CC=C(C(=CC)c1ccc(cc1)O)c1ccc(cc1)O
• InChI: InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3
• InChIKey: NFDFQCUYFHCNBW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2Z,4Z)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; 4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
• IUPAC Traditional name: 4-[(2Z,4Z)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; dienestrol
• Brand Name: Agaldog; Cycladiene; Dienoestrol BP; Dienol; Dinestrol; Dinovex; DV; Estragard; Estraguard; Estrodienol; Estroral; Follormon; Gynefollin; Hormofemin; Isodienestrol; Oestrasid; Oestrodiene; Oestrodienol; Oestroral; Oestrovis; Restrol; Retalon; Sexadien; Synestrol; Teserene; Willnestrol; para-Dien
• Synonyms: α-Dienestrol; 4,4'-[(1E,2E)-1,2-Diethylidene-1,2-ethanediyl]bis-phenol; 4,4'-(1,2-Diethylidene-1,2-ethanediyl)bis-phenol; E,E-Dienestrol; β-Dienestrol; 4,4'-[(1Z,2Z)-1,2-Diethylidene-1,2-ethanediyl]bisphenol; Z,Z-Dienestrol; 3,4-Bis(4-hydroxyphenyl)-2,4-hexadiene; Restrol; Dehydrostilbestrol; Dehydrostilboestrol; Dienesterol; Dienoestrol; Dienestrol; Dienestrol; 3,4-双(4-羟苯基)-2,4-己二烯; 双烯雌酚

Database IDs

• CAS Number: 84-17-3; 13029-44-2; 35495-11-5
• EC Number: 201-519-7
• MDL Number: MFCD00050983
• Beilstein Number: 2053694
• PubChem SID: 160964230; 24893737; 24869916
• PubChem CID: 3049; 667476
• ATC CODE: G03CB01; G03CC02
• CHEMBL: 1018
• Chemspider ID: 580857
• DrugBank ID: DB00890
• KEGG ID: D00898
• Unique Ingredient Identifier: RRW32X4U1F
• Wikipedia Title: Dienestrol

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.09934
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 4.8318524
• LogD (pH = 7.4): 4.8233767
• Log P: 4.831961
• Molar Refractivity: 84.3572 cm^3
• Polarizability: 31.886635 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.18
• LOG S: -4.33
• Solubility (Water): 1.23e-02 g/l

PROPERTIES

Physical Property

• Solubility: 3 mg/L; DMSO; Ethyl Acetate; Methanol
• Apperance: White Solid; White to Off-White Solid
• Melting Point: 183-186°C; 224-226°C (dec.)
• Hydrophobicity(logP): 5.9

Safety Information

• Storage Condition: -20°C; Amber Vial, -20°C Freezer, Under Inert Atmosphere
• RTECS: SL0580000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-62
• Safety Statements: 53-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350-H361
• GHS Precautionary statements: P201-P281-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Gloves, type P2 (EN 143) respirator cartridges

Pharmacology Properties

• Protein Bound: 50 to 80%

Product Information

• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H18O2

DETAILS

DrugBank - DB00890

• Drug Groups: approved
• Description: Dienestrol is a synthetic, non-steroidal estrogen. It is an estrogen receptor agonist. Estrogens work partly by increasing a normal clear discharge from the vagina and making the vulva and urethra healthy. Using or applying an estrogen relieves or lessens: dryness and soreness in the vagina, itching, redness, or soreness of the vulva. Conditions that are treated with vaginal estrogens include a genital skin condition (vulvar atrophy), inflammation of the vagina (atrophic vaginitis), and inflammation of the urethra (atrophic urethritis).
• Indication: For use in the treatment of atrophic vaginitis and kraurosis vulvae.
• Pharmacology: Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
• Toxicity: Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Systemic absorption and mode of action of dienestrol are undetermined.Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
• Protein Binding: 50 to 80%
• External Links: Wikipedia; RxList

Selleck Chemicals - S1858

Research Area: Endocrinology
Biological Activity:
Dienestrol(Restrol) is a synthetic, non-steroidal estrogen. It is an estrogen receptor agonist. Estrogens work partly by increasing a normal clear discharge from the vagina and making the vulva and urethra healthy. Using or applying an estrogen relieves or lessens: dryness and soreness in the vagina, itching, redness, or soreness of the vulva. Conditions that are treated with vaginal estrogens include a genital skin condition (vulvar atrophy), inflammation of the vagina (atrophic vaginitis), and inflammation of the urethra (atrophic urethritis). [1]

Sigma Aldrich - D3253

Biochem/physiol Actions
与己烯雌酚密切相关的合成雌激素化合物

Sigma Aldrich - 46190

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - D441810

A metabolite of Diethylstilbestrol.

Toronto Research Chemicals - D441815

A metabolite of Diethylstilbestrol.

REFERENCES

• http://www.drugbank.ca/drugs/DB00890
• Liehr, J.G., et al.: Steroids, 40, 713 (1982)
• Liehr, J.G., et al.: Steroids, 40, 713 (1982)