MedKoo Cat#: 584197 | Name: Sigetin

Description:

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

Sigetin affects calcium and magnesium transport in uterine smooth muscle and thus, has applications for fetal development.

Chemical Structure

Sigetin
Sigetin
CAS#3563-47-1 (potassium)

Theoretical Analysis

MedKoo Cat#: 584197

Name: Sigetin

CAS#: 3563-47-1 (potassium)

Chemical Formula: C18H20K2O6S2

Exact Mass:

Molecular Weight: 474.67

Elemental Analysis: C, 45.55; H, 4.25; K, 16.47; O, 20.22; S, 13.51

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
60252-39-3 (free acid) 3563-47-1 (potassium)
Synonym
Sigetin
IUPAC/Chemical Name
Benzenesulfonic acid, 4,4'-(1,2-diethyl-1,2-ethanediyl)bis-, dipotassium salt
InChi Key
BLMUAVFFONATJG-UHFFFAOYSA-L
InChi Code
InChI=1S/C18H22O6S2.2K/c1-3-17(13-5-9-15(10-6-13)25(19,20)21)18(4-2)14-7-11-16(12-8-14)26(22,23)24;;/h5-12,17-18H,3-4H2,1-2H3,(H,19,20,21)(H,22,23,24);;/q;2*+1/p-2
SMILES Code
CCC(C1=CC=C(S(=O)([O-])=O)C=C1)C(C2=CC=C(S(=O)([O-])=O)C=C2)CC.[K+].[K+]
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

Preparing Stock Solutions

The following data is based on the product molecular weight 474.67 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.

Recalculate based on batch purity %
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
1: Shlykov SG, Slinchenko NN, Burdyga FV, Kosterin SA. [Uterotonic action of sigetin and its effect on the Mg2+, ATP-dependent transport and stationary metabolism of Ca2+ through the myometrial sarcolemma]. Ukr Biokhim Zh (1978). 1993 May-Jun;65(3):57-65. Russian. PubMed PMID: 8291143. 2: Spiridonov BS. [Use of sigetin]. Veterinariia. 1977 Oct;(10):83-4. Russian. PubMed PMID: 919325. 3: ELAGINA LV. [INTRAVENOUS ADMINISTRATION OF SIGETIN IN THE PREVENTION OF FETAL ASPHYXIA]. Vopr Okhr Materin Det. 1965 Jan;10:58-9. Russian. PubMed PMID: 14258217. 4: TORF SF, KHROMOV-BORISOV NV. [Synthesis of sigetin (dipotassium salt of p.p'-disulfo-meso-3,4-diphenyl-hexane)]. Med Radiol. 1961 Mar;3:13-4. Russian. PubMed PMID: 13777490. 5: Stepankovskaia GK, Shinlova OP, Fomin VP, Kosterin SA, Iarotskiĭ NE. [The effect of oxytocin and sigetin on Ca2+ transport in the fraction of plasma membranes of myometrial cells]. Ukr Biokhim Zh (1978). 1989 Sep-Oct;61(5):109-12. Russian. PubMed PMID: 2588344. 6: Antonov VV. [Effect of sigetin on the sexual behavior of female rats androgenized and nonandrogenized on the 5th day of life]. Farmakol Toksikol. 1980 May-Jun;43(3):342-4. Russian. PubMed PMID: 7449975. 7: DIL'MAN VM. [Pituitary inhibitors. Effect of sigetin on the development of the uterus in prepuberal mice]. Biull Eksp Biol Med. 1959 Aug;48:104-6. Russian. PubMed PMID: 13816766. 8: Antonov VV. [Sigetin treatment of the developmental disorders induced in rabbit prenatal ontogeny by curtailment of the uteroplacental blood circulation]. Farmakol Toksikol. 1980 Jan-Feb;43(1):59-62. Russian. PubMed PMID: 7379993. 9: WU HJ. [Comparison of the mechanism of action of reserpine and certain tranquilizing agents (aminazin, diphacil, antiphenin, strophantidin and sigetin)]. Biull Eksp Biol Med. 1961 Apr;51:76-81. Russian. PubMed PMID: 13786859. 10: Garmasheva NL, Konstantinova NN, Zhakhova ZN, Bakkal TP. The effect of folliculin and sigetin on the development of the embryo and the placenta in rabbits with normal and impaired sympathetic innervation of the uterus. Am J Obstet Gynecol. 1971 Dec 15;111(8):1083-91. PubMed PMID: 5129563. 11: Barkova MKh. [The effect of glucose and sigetin on the fetus in late toxemia of pregnancy, hypertension and rhesus-factor isosensitization]. Akush Ginekol (Mosk). 1971 Oct;47(10):32-5. Russian. PubMed PMID: 5005616. 12: Ovchinnikova GA, Pigina TV. [The use of sigetin in the therapy of fetal growth retardation in the rabbit caused by uterine ischemia]. Akush Ginekol (Mosk). 1975 Feb;(2):58-60. Russian. PubMed PMID: 1217635. 13: Borin OL. [Experiment of clinical use of sigetin in the treatment of intra-uterine asphyxia of fetus]. Pediatr Akus Ginekol. 1966 Mar-Apr;2:45-8. Ukrainian. PubMed PMID: 4862015. 14: Kosheleva NG. [Use of sigetin for the prevention of perinatal mortality and morbidity after the 1st half of complicated pregnancy (experimental and clinical data)]. Akush Ginekol (Mosk). 1971 Mar;47(3):40-3. Russian. PubMed PMID: 5094022. 15: Nagy P, Csaba I. [Effect of sigetin on placenta metabolism]. Akush Ginekol (Mosk). 1982 Jan;(1):48-9. Russian. PubMed PMID: 7065368. 16: Antonov VV. [The lack of damaging effect from sigetin on the development of the reproductive system in rats]. Farmakol Toksikol. 1978 Jun-Aug;41(4):458-61. Russian. PubMed PMID: 668873. 17: Svergun VT. [Effect of sigetin on the concentration of triglycerides and cholesterol in rat blood and liver]. Biull Eksp Biol Med. 1979 Feb;87(2):151-3. Russian. PubMed PMID: 420935. 18: Osipova EP. [Effect of sigetin and glucose injections during pregnancy on the resistance to anoxia of premature normal growth and growth retarded fetuses (experimental study)]. Akush Ginekol (Mosk). 1985 Jun;(6):29-30. Russian. PubMed PMID: 2932009. 19: Kishsh Ch, Bogdan Sh, Benë T. [Treatment of climacteric disorders with sigetin]. Akush Ginekol (Mosk). 1975 Oct;(10):61-2. Russian. PubMed PMID: 1211564. 20: Chistiakov GV. [Partusisten and sigetin treatment of hypotrophy of female rabbit fetuses in experimental disorders of utero-placental circulation]. Vestn Akad Med Nauk SSSR. 1981;(6):36-8. Russian. PubMed PMID: 6117162.