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50-56-6

Basic Information
CAS No.: 50-56-6
Name: Oxytocin
Article Data: 38
Cas Database
Molecular Structure:
Molecular Structure of 50-56-6 (Oxytocin)
Formula: C43H66N12O12S2
Molecular Weight: 1007.2
Synonyms: 3-Isoleucine-8-leucine vasopressin;Alpha-hypophamine;Atonin O;Di-sipidin;Endopituitrina;Hyphotocin;Intertocine S;Nobitocin S;Orasthin;Partocon;Perlacton;Pitocin;Piton S;Presoxin;Synpitan;Synpitan forte;Synthetic oxytocin;Syntocin;Syntocinon;Syntocinone;Uteracon;Vasopressin, 3-L-isoleucine-8-L-leucine-;[1-Hemicystine]-oxytocin;a-Hypophamine;Oxytocin Acetate;Oxytocin Acetate USP30;
EINECS: 200-048-4
Density: 1.27 g/cm3
Melting Point: 192-194 °C
Boiling Point: 1533.3 °C at 760 mmHg
Flash Point: 881.1 °C
Solubility: Soluble in water.
Appearance: White Solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information: UN 3249
PSA: 450.13000
LogP: 1.55630
Synthetic route
151937-33-6

1,Cys(SH)6>-oxytocin

50-56-6

oxytocin

Conditions
ConditionsYield
Stage #1: 1,Cys(SH)6>-oxytocin With iodine In acetic acid at 20℃;
Stage #2: With isoascorbic acid In acetic acid
98.5%
With dimethyl sulfoxide; methoxybenzene; trifluoroacetic acid for 1h;69 % Chromat.
17912-60-6

H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2

50-56-6

oxytocin

Conditions
ConditionsYield
With [Pt(en)2Cl2](2+); ethylenediaminetetraacetic acid; sodium chloride In phosphate buffer pH=4 - 7;98%
With molybdophosphoric acid hydrate In dimethyl sulfoxide at 20℃; for 24h;90%
With ammonium hydroxide; acetic acid In water for 6h; pH=7;63%

Boc-Cys(Acm)(O)-Tyr-Ile-Gln-Asn-Cys(MBzl)-Pro-Leu-Gly-NH2

50-56-6

oxytocin

Conditions
ConditionsYield
With dimethylsulfide In trifluoroacetic acid 1.) ice bath, 60 min; 2.) 25 deg C, 60 min;86%

C90H109N12O14PolS2

50-56-6

oxytocin

Conditions
ConditionsYield
With chlorotriisopropylsilane; trifluoroacetic acid In water for 0.5h; Rink Amide AM resin;85.22%

Boc-Cys(MBzl)-Tyr-Ile-Gln-Asn-Cys(MBzl)-Pro-Leu-Gly-NH2

50-56-6

oxytocin

Conditions
ConditionsYield
With dimethyl sulfoxide; methoxybenzene; trifluoroacetic acid at 25℃; for 12h;73.5%
133383-08-1

1,6>-oxytocin

50-56-6

oxytocin

Conditions
ConditionsYield
With chloro-trimethyl-silane; 1,1'-sulfinylbisbenzene; methoxybenzene; trifluoroacetic acid at 25℃; for 0.166667h;69%
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

35661-60-0

Fmoc-Leu-OH

71989-31-6

Fmoc-Pro-OH

71989-23-6

Fmoc-Ile-OH

71989-38-3

Fmoc-Tyr(tBu)-OH

132388-59-1

L-Asn(Trt)

132327-80-1

Fmoc-L-Gln(Trt)-OH

73724-43-3

3-[(1,1-dimethylethyl)dithio]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

50-56-6

oxytocin

Conditions
ConditionsYield
Stage #1: 3-[(1,1-dimethylethyl)dithio]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Automated synthesizer;
Stage #2: With piperidine In N,N-dimethyl-formamide Inert atmosphere; Automated synthesizer;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; Fmoc-Pro-OH; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; 3-[(1,1-dimethylethyl)dithio]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine Reagent/catalyst; Further stages;
65%
104523-34-4

1,6>-oxytocin

50-56-6

oxytocin

Conditions
ConditionsYield
With chloro-trimethyl-silane; 1,1'-sulfinylbisbenzene; methoxybenzene; trifluoroacetic acid at 25℃; for 0.166667h;64%
104523-33-3

1,6>-oxytocin

50-56-6

oxytocin

Conditions
ConditionsYield
With chloro-trimethyl-silane; 1,1'-sulfinylbisbenzene; methoxybenzene; trifluoroacetic acid at 25℃; for 0.166667h;56%
With hydrogenchloride; silver trifluoromethanesulfonate; methoxybenzene 1.) TFA, 4 deg C, 1.5 h, 2.) DMSO, r.t., 7 h; Yield given. Multistep reaction;
111193-50-1

Z(OMe)-Cys(MBzl)-Tyr-Ile-Gln-Asn-Cys(MBzl)-Pro-Leu-Gly-NH2

50-56-6

oxytocin

Conditions
ConditionsYield
With thallium(III) trifluoroacetate In trifluoroacetic acid for 1h;27%
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h;27%
Raw Materials
27610-07-7
Downstream Products
407-25-0
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Specification

1. Introduction of Oxytocin
Oxytocin is a white powder. The IUPAC Name of this chemical is (2S)-1-[(1R,4S,7S,10S,13S,16R)-16-Amino-4-(2-amino-2-oxoethyl)-7-(3-amino-3-oxopropyl)-10-[(2S)-butan-2-yl]-13-[(4-hydroxyphenyl)methyl]-3,6,9,12,15-pentaoxo-18,19-dithia-2,5,8,11,14-pentazacycloicosane-1-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide. Besides, Oxytocin belongs the product categories which is Amino Acid Derivatives; Organics; Amino Acids 13C, 2H, 15N; Peptide; Amino Acids & Derivatives; Intermediates & Fine Chemicals; Pharmaceuticals; Vasopressin and Oxytocin receptor; Peptide Receptors.

The Classification Code of Oxytocin is Drug / Therapeutic Agent; Hormone; Human Data; Oxytocic; Oxytocics; Reproductive Control Agents; Reproductive Effect. Furthermore, Oxytocin can soluble in water.

2. Properties of Oxytocin
Physical properties about Oxytocin are:
(1)Melting point: 192-194 °C; (2)Storage temp.:  2-8 °C; (3)Merck:  13,7049; (4)Density: 1.27 g/cm3; (5)Flash Point: 881.1 °C;(6)Index of Refraction: 1.554; (7)Surface Tension: 51.8 dyne/cm; (8)Appearance: lyophilized powder; (9)Enthalpy of Vaporization: 245.93 kJ/mol; (10)Boiling Point: 1533.3 °C at 760 mmHg; (11)XLogP3-AA: -2.6; (12)H-Bond Donor: 12; (13)H-Bond Acceptor: 15.

3. Structure Descriptors of Oxytocin
(1)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)N)CC(=O)N)CCC(=O)N
(2)Isomeric SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N
[C@H](C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
(3)InChI: InChI=1S/C43H66N12O12S2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1
(4)InChIKey: XNOPRXBHLZRZKH-DSZYJQQASA-N
(5)Smiles: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)Cc2ccc(cc2)O)N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N

4. Toxicity of Oxytocin

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 5800ug/kg (5.8mg/kg)   Drugs in Japan Vol. 6, Pg. 151, 1982.
mouse LD50 oral > 514mg/kg (514mg/kg)   Drugs in Japan Vol. -, Pg. 230, 1990.
mouse LD50 subcutaneous > 514mg/kg (514mg/kg)   Drugs in Japan Vol. -, Pg. 230, 1990.
rat LD50 intravenous 2275ug/kg (2.275mg/kg)   Drugs in Japan Vol. -, Pg. 230, 1990.
rat LD50 oral > 20520ug/kg (20.52mg/kg)   Drugs in Japan Vol. -, Pg. 230, 1990.
rat LD50 subcutaneous > 20520ug/kg (20.52mg/kg)   Drugs in Japan Vol. -, Pg. 230, 1990.

Or

1.    

ivn-mus LD50:5800 µg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),151.

5. Physical Properties of Oxytocin

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -6.270 (none)   EST
Atmospheric OH Rate Constant 5.33E-10 cm3/molecule-sec 25 EST

6. Safety information of Oxytocin
Poison by intravenous route. Experimental reproductive effects. A pituitary hormone which stimulates uterine contraction and milk production. The principal uterus-contracting and lactation-stimulating hormone of the posterior pituitary gland. Note: Unlike vasopressin which occurs in at least two forms, Oxytocin from beef and hog sources shows no difference in amino acid composition. When heated to decomposition it emits toxic fumes of SOx and NOx.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
RIDADR: 3249
WGK Germany: 3
F: 3-8-10-23
HazardClass: 6.1(a)
PackingGroup: II
RTECS: RS7534000

7. Uses of Oxytocin
Oxytocin (CAS NO.50-56-6) is the principal uterus-contracting and lactation-stimulating hormone of the posterior pituitary gland.It is released in large amounts after distension of the cervix and vagina during labor, and after stimulation of the nipples, facilitating birth and breastfeeding, respectively. It is a mammalian hormone that also acts as a neurotransmitter in the brain.