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Key Documents

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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J W Liu et al.
Endocrinology, 134(1), 114-118 (1994-01-01)
Oxytocin (OT) and arginine vasopressin (AVP) have been reported to release PRL both in vivo and in vitro. The objectives of this study were 1) to compare the potencies of the PRL-releasing activities of OT and TRH using cultured anterior
J Hlavácek et al.
Journal of peptide science : an official publication of the European Peptide Society, 7(7), 349-357 (2001-08-10)
A few solid phase and solution approaches of good repute were applied in parallel with the aim to provide optimized routes to Boc- and Fmoc-tocinoic acid (3a and 3c) and the corresponding Tyr(Bu(t)) derivatives (3b and 3d). Boc-tocinoic acid is
U Roy et al.
International journal of peptide and protein research, 28(2), 154-162 (1986-08-01)
Tocinoic acid analogs with penicillamine in place of one or both of the cysteine residues have been studied and [1-beta-mercaptopropionic acid, 6-penicillamine] tocinoic acid (dPen6TA) and [1-beta,beta-dimethyl-beta-mercaptopropionic acid, 6-penicillamine] tocinoic acid (dPen1Pen6TA) have been synthesized in solution. Biological activities of
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)
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

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