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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:
34330-23-9
Molecular Weight:
740.85
MDL number:
MFCD00076737
UNSPSC Code:
51111800
PubChem Substance ID:
24900110

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M A Lang et al.
The American journal of physiology, 251(1 Pt 2), R77-R81 (1986-07-01)
To characterize the V2 receptor (for antidiuretic hormone), we have studied the effect of a number of neurohypophysial hormone analogues on cyclic AMP (cAMP) accumulation and short-circuit current in cultured epithelia formed by A6 cells. A6 is the designation of
A P Da Costa et al.
Journal of neuroendocrinology, 8(3), 163-177 (1996-03-01)
Oxytocin (OT) release within the brain is thought to play a major role in inducing maternal behaviour in a number of mammalian species but little is known about the sites of release which are important in this respect. We have
A V Sirotkin et al.
Fiziologicheskii zhurnal SSSR imeni I. M. Sechenova, 68(1), 112-115 (1982-01-01)
Administration of arginin-vasotocin, oxytocin and their fragments had no effect on corticosterone content in the blood plasma of 10-month chickens whereas in 20 and 30-day chickens arginin-vasotocin and its terminal fragment: amid of prolyl-arginil-glycil, considerably increased the corticosterone content. The
C Fotsch et al.
Bioorganic & medicinal chemistry letters, 9(15), 2125-2130 (1999-08-28)
On-resin macrocyclization via an SNAr reaction is employed in the synthesis of tocinoic acid analogs. Specifically, an N-terminal nitrofluorobenzene is attacked by a nucleophilic C-terminal sidechain. The remaining nitro group can be reduced and acylated. NMR is used to compare
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
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