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T3149

Sigma-Aldrich

Tocinoic acid

≥97% (HPLC)

Synonym(s):

[Ile3]-Pressinoic acid

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About This Item

Empirical Formula (Hill Notation):
C30H44N8O10S2
CAS Number:
Molecular Weight:
740.85
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:

Assay

≥97% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

storage temp.

−20°C

SMILES string

CCC(C)C1NC(=O)C(Cc2ccc(O)cc2)NC(=O)C(N)CSSCC(NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC1=O)C(O)=O

InChI

1S/C30H44N8O10S2/c1-3-14(2)24-29(46)34-18(8-9-22(32)40)26(43)36-20(11-23(33)41)27(44)37-21(30(47)48)13-50-49-12-17(31)25(42)35-19(28(45)38-24)10-15-4-6-16(39)7-5-15/h4-7,14,17-21,24,39H,3,8-13,31H2,1-2H3,(H2,32,40)(H2,33,41)(H,34,46)(H,35,42)(H,36,43)(H,37,44)(H,38,45)(H,47,48)

InChI key

ITRWUGOBSKHPTA-UHFFFAOYSA-N

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Amino Acid Sequence

Cys-Tyr-Ile-Gln-Asn-Cys [Disulfide bridge: 1-6]

Application

Tocinoic acid is an oxytocin receptor antagonist and is used to study effects of oxytocin and 5-HT1A receptors on the prosocial effects of 3,4 methylenedioxymethamphetamine (MDMA; ecstasy). It can also be used as a test compound for studying whether the release of protein disulfide isomerase activity is stimulated by activated platelets or not.

Biochem/physiol Actions

Tocinoic acid contains the ring structure of oxytocin that inhibits the release of melanocyte-stimulating hormones (MSH) the rat pituitary in vitro.

Other Notes

N-terminal hexapeptide fragment of oxytocin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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D Despeyroux et al.
Rapid communications in mass spectrometry : RCM, 5(4), 156-159 (1991-04-01)
A method has been developed for the determination of the amino-acid sequence of a cyclic peptide containing cystine. It is based on the reduction of the peptide in a reductive matrix prior to ionization by fast-atom bombardment. The amino-acid sequence
M Salzet et al.
Brain research, 601(1-2), 173-184 (1993-01-22)
A large number of oxytocin (OT)-like neurons were detected in the sex segmental ganglia (SG5, SG6) of three species of leeches belonging to different orders: Theromyzon tessulatum, Hirudo medicinalis and Erpobdella octoculata. In this latter species, an epitope close to
V S Ananthanarayanan et al.
Biopolymers, 40(5), 433-443 (1996-01-01)
Extracellular Ca2+ is required for the action of oxytocin and both the hormone and its receptor have binding sites for divalent metal cations. To characterize the cation-bound form of oxytocin, we monitored the binding of Ca2+ and Mg2+ to oxytocin
Lei Zhang et al.
Journal of pharmaceutical sciences, 98(9), 3312-3318 (2008-08-08)
Thiol/disulfide interchange is one of the most common routes of aggregation of lyophilized protein drug products, but the mechanisms of the reaction in the solid state have not been established. Here, we report perturbations in thiol/disulfide interchange upon lyophilization, using
Comparative MSH release-inhibiting activities of tocinoic acid (the ring of oxytocin), and L-pro-L-leu-gly-NH 2 (the side chain of oxytocin).
A Bower et al.
Biochemical and biophysical research communications, 45(5), 1185-1191 (1971-12-03)

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