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Merck
CN

T3149

Tocinoic acid

≥97% (HPLC)

Synonym(s):

[Ile3]-Pressinoic acid

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About This Item

Empirical Formula (Hill Notation):
C30H44N8O10S2
CAS Number:
34330-23-9
Molecular Weight:
740.85
UNSPSC Code:
51111800
PubChem Substance ID:
24900110
MDL number:
MFCD00076737

Key Documents

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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)

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 key

ITRWUGOBSKHPTA-UHFFFAOYSA-N

assay

≥97% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

storage temp.

−20°C

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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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
030M1465
079K1166
059K1114
118K1201
057K1504

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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
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
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
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
Jun Zheng et al.
American journal of physiology. Gastrointestinal and liver physiology, 299(4), G946-G953 (2010-08-07)
Accumulation of continuous life stress (chronic stress) often causes gastric symptoms. Although central oxytocin has antistress effects, the role of central oxytocin in stress-induced gastric dysmotility remains unknown. Solid gastric emptying was measured in rats receiving acute restraint stress, 5
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