Dienestrol
Catalog Number: BT-264490
CAS Number: 84-17-3
Molecular Formula: C18H18O2
Molecular Weight: 266.3 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Dienestrol is a synthetic nonsteroidal estrogen that was first synthesized in the 1940s. It is used in medical, environmental, and industrial research due to its potent estrogenic activity. This paper will discuss the method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges of Dienestrol.
Properties
CAS Number
84-17-3
Product Name
Dienestrol
IUPAC Name
4-[(2E,4E)-4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
Molecular Formula
C18H18O2
Molecular Weight
266.3 g/mol
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/b17-3+,18-4+
InChI Key
NFDFQCUYFHCNBW-SCGPFSFSSA-N
SMILES
CC=C(C1=CC=C(C=C1)O)C(=CC)C2=CC=C(C=C2)O
Solubility
3 mg/L (at 37 °C)
FREELY SOL IN ALC, METHANOL, ETHER, ACETONE, PROPYLENE GLYCOL; SOL IN CHLOROFORM, AQ SOLN OF ALKALI HYDROXIDES; SOLUBLE IN VEGETABLE OILS AFTER WARMING, BUT CRYSTALLIZES OUT ON STANDING; PRACTICALLY INSOL IN WATER, DIL ACIDS .
SOL IN FIXED OILS.
FREELY SOL IN ALC, METHANOL, ETHER, ACETONE, PROPYLENE GLYCOL; SOL IN CHLOROFORM, AQ SOLN OF ALKALI HYDROXIDES; SOLUBLE IN VEGETABLE OILS AFTER WARMING, BUT CRYSTALLIZES OUT ON STANDING; PRACTICALLY INSOL IN WATER, DIL ACIDS .
SOL IN FIXED OILS.
Synonyms
4,4'-(Diethylideneethylene)diphenol
Dienestrol
Dienestrol, (E,E)-Isomer
Dienestrol, (Z,E)-Isomer
Dienestrol, (Z,Z)-Isomer
Dienoestrol
Oestrasid
Ortho Dienestrol
Synestrol
Dienestrol
Dienestrol, (E,E)-Isomer
Dienestrol, (Z,E)-Isomer
Dienestrol, (Z,Z)-Isomer
Dienoestrol
Oestrasid
Ortho Dienestrol
Synestrol
Canonical SMILES
CC=C(C1=CC=C(C=C1)O)C(=CC)C2=CC=C(C=C2)O
Isomeric SMILES
C/C=C(\C1=CC=C(C=C1)O)/C(=C\C)/C2=CC=C(C=C2)O
Method of Synthesis or Extraction
Dienestrol can be synthesized by several methods, including the reaction of estrone with ethylene oxide or the reaction of estradiol with diethyl sulfate. The efficiency and yield of each method vary, with the estrone-ethylene oxide method being the most efficient and yielding the highest amount of Dienestrol. However, the use of ethylene oxide and diethyl sulfate raises environmental and safety concerns due to their toxicity and potential carcinogenicity.
Chemical Structure and Biological Activity
Dienestrol has a chemical structure similar to that of natural estrogens, with two hydroxyl groups on the A and B rings. It binds to estrogen receptors and activates them, leading to the transcription of estrogen-responsive genes. Dienestrol has a higher affinity for estrogen receptors than natural estrogens, making it a potent estrogenic compound. It has been shown to have a variety of biological activities, including promoting the growth of breast cancer cells and reducing bone resorption.
Biological Effects
Dienestrol has been shown to have both therapeutic and toxic effects. It can promote the growth of breast cancer cells and increase the risk of endometrial cancer. However, it has also been used to treat menopausal symptoms and osteoporosis. In addition, Dienestrol has been shown to affect cell function and signal transduction, leading to changes in gene expression and cellular metabolism.
Applications
Dienestrol has been used in medical research to develop drugs for the treatment of menopausal symptoms and osteoporosis. It has also been used in clinical trials to evaluate its efficacy and safety. In environmental research, Dienestrol has been studied for its effects on ecosystems and its role in pollution management. In industrial research, it has been used in manufacturing processes to improve product quality and efficiency. However, the use of Dienestrol raises health and safety concerns due to its potential toxicity and carcinogenicity.
Future Perspectives and Challenges
The use of Dienestrol in scientific research is limited by its potential toxicity and carcinogenicity. Possible solutions and improvements include the development of safer and more efficient methods of synthesis or extraction and the identification of alternative compounds with similar biological activity. Future trends and prospects in the application of Dienestrol in scientific research include the development of new drugs for the treatment of menopausal symptoms and osteoporosis and the study of its effects on ecosystems and pollution management.
Conclusion:
Dienestrol is a synthetic nonsteroidal estrogen that has been used in medical, environmental, and industrial research due to its potent estrogenic activity. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges have been discussed in this paper. The use of Dienestrol raises health and safety concerns, and further research is needed to develop safer and more efficient methods of synthesis or extraction and to identify alternative compounds with similar biological activity.
Conclusion:
Dienestrol is a synthetic nonsteroidal estrogen that has been used in medical, environmental, and industrial research due to its potent estrogenic activity. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges have been discussed in this paper. The use of Dienestrol raises health and safety concerns, and further research is needed to develop safer and more efficient methods of synthesis or extraction and to identify alternative compounds with similar biological activity.
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