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50-56-6

Basic Information
CAS No.: 50-56-6
Name: Oxytocin
Molecular Structure:
Molecular Structure of 50-56-6 (Oxytocin)
Formula: C43H66N12O12S2
Molecular Weight: 1007.33 g/mol
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%

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

50-56-6

oxytocin

Conditions
ConditionsYield
With thallium(III) trifluoroacetate In trifluoroacetic acid for 1h;22%

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

50-56-6

oxytocin

Conditions
ConditionsYield
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h;22%
35661-60-0

Fmoc-Leu-OH

67436-13-9

(R)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

115057-30-2

{4-[[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyrylamino]-(4-methoxy-phenyl)-methyl]-2-methyl-phenoxy}-acetic acid

71989-31-6

Fmoc-Pro-OH

50-56-6

oxytocin

Conditions
ConditionsYield
solid phase synthesis; the next amino acids are: Fmoc-Asn-OH, Fmoc-Gln-OH, Fmoc-Ile-OH and Fmoc-Tyr(tBu)-OH; Yield given. Multistep reaction;
5068-30-4

S,S'-Dihydrooxytocin hydrochloride

50-56-6

oxytocin

Conditions
ConditionsYield
In water for 360h;
Conditions
ConditionsYield
With potassium hexacyanoperferrate; sodium 1.) fl. NH3; Yield given. Multistep reaction;
78221-69-9

benzyloxycarbonyl-S-(2,4,6-trimethylbenzyl)-L-cysteinyl-O-tert-butyl-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparaginyl-S-(2,4,6-trimethylbenzyl)-L-cysteinyl-L-prolyl-L-leucyl-glycine amide

50-56-6

oxytocin

Conditions
ConditionsYield
With air; hydrogen fluoride; methoxybenzene 1) 0 degC, 30 min, 2) H2O, 1 h; Yield given. Multistep reaction;

1,6>-oxytocin

50-56-6

oxytocin

Conditions
ConditionsYield
With dimethyl sulfoxide; methoxybenzene; trifluoroacetic acid for 2h;86 % Chromat.

C71H88N12O12S2

50-56-6

oxytocin

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide
17912-60-6

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

64806-05-9

Captopril disulfide

A

50-56-6

oxytocin

B

62571-86-2

captopril

Conditions
ConditionsYield
In water at 25℃; for 5h; Equilibrium constant; pH 7.0;

C52H81N13O15S3

C52H81N13O15S3

A

50-56-6

oxytocin

B

62571-86-2

captopril

Conditions
ConditionsYield
In water at 25℃; for 5h; Rate constant; Equilibrium constant; pH 7.0;

C48H77N13O14S3

C48H77N13O14S3

A

52-66-4

DL-Penicillamin

B

50-56-6

oxytocin

Conditions
ConditionsYield
In water at 25℃; for 5h; Rate constant; Equilibrium constant; pH 7.0;
141437-69-6

α-Boc,Cys(t-Bu)1,6>-oxytocin

50-56-6

oxytocin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / TFA, anisole / 1 h
2: 64 percent / TFA, Me3SiCl, PhS(O)Ph, anisole / 0.17 h / 25 °C
View Scheme

Nα-tert-Butoxycarbonyl-S,S'-dibenzyloxytocin

50-56-6

oxytocin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.45 g / metallic sodium / liquid ammonia / Heating
2: 0.408 g / 2.58 N HCl / acetic acid / 0.07 h
3: H2O / 360 h
View Scheme

Nα-BOC-S,S'-dihydrooxytocin

50-56-6

oxytocin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.408 g / 2.58 N HCl / acetic acid / 0.07 h
2: H2O / 360 h
View Scheme
1391105-08-0

Boc-Cys(Trt)-Pro-Leu-Gly-OMe

50-56-6

oxytocin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ammonia / methanol / 24 h / Inert atmosphere
2.1: chlorotriisopropylsilane; water; trifluoroacetic acid; phenol / 1.5 h / 20 °C / Inert atmosphere
3.1: sodium dihydrogenphosphate; tris-(2-carboxyethyl)-phosphine hydrochloride / pH 7.2 / Inert atmosphere
3.2: Inert atmosphere
4.1: ammonium hydroxide; acetic acid / water / 6 h / pH 7
View Scheme
41089-31-0

H-Cys-Pro-Leu-Gly-NH2

50-56-6

oxytocin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium dihydrogenphosphate; tris-(2-carboxyethyl)-phosphine hydrochloride / pH 7.2 / Inert atmosphere
1.2: Inert atmosphere
2.1: ammonium hydroxide; acetic acid / water / 6 h / pH 7
View Scheme
27610-07-7, 62188-56-1

(S)-methyl 2-(2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)acetate

50-56-6

oxytocin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: trifluoroacetic acid / chloroform / 1 h / Inert atmosphere
2.1: tert-butylisonitrile; benzotriazol-1-ol / chloroform / 20 °C / Inert atmosphere
3.1: trifluoroacetic acid / chloroform / 1 h / Inert atmosphere
4.1: tert-butylisonitrile; benzotriazol-1-ol / chloroform / 20 °C / Inert atmosphere
5.1: ammonia / methanol / 24 h / Inert atmosphere
6.1: chlorotriisopropylsilane; water; trifluoroacetic acid; phenol / 1.5 h / 20 °C / Inert atmosphere
7.1: sodium dihydrogenphosphate; tris-(2-carboxyethyl)-phosphine hydrochloride / pH 7.2 / Inert atmosphere
7.2: Inert atmosphere
8.1: ammonium hydroxide; acetic acid / water / 6 h / pH 7
View Scheme
27560-15-2, 119621-63-5, 120089-68-1

methyl 2-(2-amino-4-methylpentanamido)acetate

50-56-6

oxytocin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tert-butylisonitrile; benzotriazol-1-ol / chloroform / 20 °C / Inert atmosphere
2.1: trifluoroacetic acid / chloroform / 1 h / Inert atmosphere
3.1: tert-butylisonitrile; benzotriazol-1-ol / chloroform / 20 °C / Inert atmosphere
4.1: ammonia / methanol / 24 h / Inert atmosphere
5.1: chlorotriisopropylsilane; water; trifluoroacetic acid; phenol / 1.5 h / 20 °C / Inert atmosphere
6.1: sodium dihydrogenphosphate; tris-(2-carboxyethyl)-phosphine hydrochloride / pH 7.2 / Inert atmosphere
6.2: Inert atmosphere
7.1: ammonium hydroxide; acetic acid / water / 6 h / pH 7
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: trifluoroacetic acid / chloroform / 1 h / Inert atmosphere
2.1: tert-butylisonitrile; benzotriazol-1-ol / chloroform / 20 °C / Inert atmosphere
3.1: ammonia / methanol / 24 h / Inert atmosphere
4.1: chlorotriisopropylsilane; water; trifluoroacetic acid; phenol / 1.5 h / 20 °C / Inert atmosphere
5.1: sodium dihydrogenphosphate; tris-(2-carboxyethyl)-phosphine hydrochloride / pH 7.2 / Inert atmosphere
5.2: Inert atmosphere
6.1: ammonium hydroxide; acetic acid / water / 6 h / pH 7
View Scheme
623-65-4

palmitic anhydride

50-56-6

oxytocin

N-palmitoyloxytocin

Conditions
ConditionsYield
With triethylamine In dichloromethane; N,N-dimethyl-formamide for 3h;96%
50-56-6

oxytocin

769884-11-9

mono-6-deoxy-6-carboxy-β-cyclodextrin

1024982-27-1

C85H132N12O47S2

Conditions
ConditionsYield
Stage #1: mono-6-deoxy-6-carboxy-β-cyclodextrin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 4℃; for 1h;
Stage #2: oxytocin In N,N-dimethyl-formamide at 20℃; for 48h; Further stages.;
30%
52-90-4

L-Cysteine

50-56-6

oxytocin

A

56-89-3

L-cystine

B

17912-60-6

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

Conditions
ConditionsYield
With potassium chloride In water at 25℃; Equilibrium constant; Rate constant; pH = 7;
70-18-8

GLUTATHIONE

50-56-6

oxytocin

A

27025-41-8

Oxidized glutathione

B

17912-60-6

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

Conditions
ConditionsYield
With potassium chloride In water at 25℃; Equilibrium constant; Rate constant; pH = 7;
50-56-6

oxytocin

60-24-2

2-hydroxyethanethiol

C45H72N12O13S2

Conditions
ConditionsYield
at 80℃; Kinetics;
52-66-4

DL-Penicillamin

50-56-6

oxytocin

A

C48H77N13O14S3

B

C48H77N13O14S3

Conditions
ConditionsYield
In water at 25℃; for 5h; Rate constant; Equilibrium constant; pH 7.0;
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.

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