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Oxytocinoic acid

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Oxytocinoic acid is an analog of Oxytocin, which is a mammalian neurohypophysial hormone used as a vasodilator agent.

Category

Others

Catalog number

BAT-015804

CAS number

4248-64-0

Molecular Formula

C43H65N11O13S2

Molecular Weight

1008.18

Specification
Reference Reading

IUPAC Name

2-[[(2S)-2-[[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]acetic acid

Synonyms

9-Glycineoxytocin; 9-Deamidooxytocin; Oxytocin free acid; Oxytocin, 9-glycine-; Oxytocinic acid; L-cysteinyl-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparagyl-L-cysteinyl-L-prolyl-L-leucyl-glycine (1->6)-disulfide; H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-OH (Disulfide bridge: Cys1-Cys6); Oxytocic Acid

Related CAS

24346-32-5 (Deleted CAS) 2101865-21-6 (Deleted CAS)

Appearance

White to Off-white Lyophilized Powder

Purity

≥95%

Density

1.281±0.06 g/cm3

Boiling Point

1522.6±65.0°C at 760 mmHg

Sequence

CYIQNCPLG (Disulfide bridge: Cys1-Cys6)

Storage

Store at -20°C, protect from light and moisture

Solubility

Soluble in DMSO, Water

InChI

InChI=1S/C43H65N11O13S2/c1-5-22(4)35-42(66)48-26(12-13-32(45)56)38(62)50-29(17-33(46)57)39(63)52-30(20-69-68-19-25(44)36(60)49-28(40(64)53-35)16-23-8-10-24(55)11-9-23)43(67)54-14-6-7-31(54)41(65)51-27(15-21(2)3)37(61)47-18-34(58)59/h8-11,21-22,25-31,35,55H,5-7,12-20,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,61)(H,48,66)(H,49,60)(H,50,62)(H,51,65)(H,52,63)(H,53,64)(H,58,59)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1

InChI Key

NFBCSRNZYJJWNB-DSZYJQQASA-N

Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)O)CC(=O)N)CCC(=O)N

3. Effect of changing the COOH-terminal amide group present in the hydrophilic cluster of oxytocin to dimethylamide

Y F Ting, C W Smith, G L Stahl, R Walter, P Cordopatis, D Theodoropoulos J Med Chem. 1980 Jun;23(6):693-5. doi: 10.1021/jm00180a026.

Oxytocinoic acid dimethylamide was synthesized by stepwise solution techniques as part of an ongoing evaluation of the effects on the biological activity of oxytocin caused by individually changing the groups that comprises the hydrophilic surface of the hormone to more hydrophobic and more bulky groups. The analogue exhibited approximately 3% of the potency of oxytocin in the in vitro uterotonic assay. In addition, it possesses potencies of less than 0.07, less than 0.01, and 0.096 unit/mg in the avian vasodepressor, rat pressor, and rat antidiuretic assays, respectively. In the in vitro uterotonic assay, oxytocinoic acid dimethylamide showed a reduced affinity for the oxytocin receptor, a nonparallel dose-response relationship, and most importantly a reduced intrinsic activity as compared to oxytocin. The results suggest that the replacement of the protons of the primary carboxyamide of Gly9-NH2 of oxytocin by methyl groups displaces the active elements from the orientation for obtaining maximal intrinsic activity in the isolated rat uterus.