1,Cys(SH)6>-oxytocin
oxytocin
Conditions | Yield |
---|---|
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. |
H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2
oxytocin
Conditions | Yield |
---|---|
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% |
oxytocin
Conditions | Yield |
---|---|
With dimethylsulfide In trifluoroacetic acid 1.) ice bath, 60 min; 2.) 25 deg C, 60 min; | 86% |
oxytocin
Conditions | Yield |
---|---|
With chlorotriisopropylsilane; trifluoroacetic acid In water for 0.5h; Rink Amide AM resin; | 85.22% |
oxytocin
Conditions | Yield |
---|---|
With dimethyl sulfoxide; methoxybenzene; trifluoroacetic acid at 25℃; for 12h; | 73.5% |
1,6>-oxytocin
oxytocin
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; 1,1'-sulfinylbisbenzene; methoxybenzene; trifluoroacetic acid at 25℃; for 0.166667h; | 69% |
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
oxytocin
Conditions | Yield |
---|---|
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% |
1,6>-oxytocin
oxytocin
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; 1,1'-sulfinylbisbenzene; methoxybenzene; trifluoroacetic acid at 25℃; for 0.166667h; | 64% |
1,6>-oxytocin
oxytocin
Conditions | Yield |
---|---|
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; |
Z(OMe)-Cys(MBzl)-Tyr-Ile-Gln-Asn-Cys(MBzl)-Pro-Leu-Gly-NH2
oxytocin
Conditions | Yield |
---|---|
With thallium(III) trifluoroacetate In trifluoroacetic acid for 1h; | 27% |
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h; | 27% |
oxytocin
Conditions | Yield |
---|---|
With thallium(III) trifluoroacetate In trifluoroacetic acid for 1h; | 22% |
oxytocin
Conditions | Yield |
---|---|
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h; | 22% |
Fmoc-Leu-OH
(R)-3-tert-Butylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
{4-[[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyrylamino]-(4-methoxy-phenyl)-methyl]-2-methyl-phenoxy}-acetic acid
Fmoc-Pro-OH
oxytocin
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
In water for 360h; |
Z-Cys(Bzl)-Tyr-Ile-Gln-Asn-Cys(Bzl)-Pro-Leu-Gly-NH2
oxytocin
Conditions | Yield |
---|---|
With potassium hexacyanoperferrate; sodium 1.) fl. NH3; Yield given. Multistep reaction; |
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
oxytocin
Conditions | Yield |
---|---|
With air; hydrogen fluoride; methoxybenzene 1) 0 degC, 30 min, 2) H2O, 1 h; Yield given. Multistep reaction; |
oxytocin
Conditions | Yield |
---|---|
With dimethyl sulfoxide; methoxybenzene; trifluoroacetic acid for 2h; | 86 % Chromat. |
oxytocin
Conditions | Yield |
---|---|
With piperidine In N,N-dimethyl-formamide |
H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2
Captopril disulfide
A
oxytocin
B
captopril
Conditions | Yield |
---|---|
In water at 25℃; for 5h; Equilibrium constant; pH 7.0; |
Conditions | Yield |
---|---|
In water at 25℃; for 5h; Rate constant; Equilibrium constant; pH 7.0; |
Conditions | Yield |
---|---|
In water at 25℃; for 5h; Rate constant; Equilibrium constant; pH 7.0; |
α-Boc,Cys(t-Bu)1,6>-oxytocin
oxytocin
Conditions | Yield |
---|---|
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 |
oxytocin
Conditions | Yield |
---|---|
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 |
oxytocin
Conditions | Yield |
---|---|
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 |
Boc-Cys(Trt)-Pro-Leu-Gly-OMe
oxytocin
Conditions | Yield |
---|---|
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 |
H-Cys-Pro-Leu-Gly-NH2
oxytocin
Conditions | Yield |
---|---|
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 |
(S)-methyl 2-(2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)acetate
oxytocin
Conditions | Yield |
---|---|
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 |
methyl 2-(2-amino-4-methylpentanamido)acetate
oxytocin
Conditions | Yield |
---|---|
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 |
Boc-Pro-Leu-Gly-OMe
oxytocin
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; N,N-dimethyl-formamide for 3h; | 96% |
Conditions | Yield |
---|---|
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% |
L-Cysteine
oxytocin
A
L-cystine
B
H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2
Conditions | Yield |
---|---|
With potassium chloride In water at 25℃; Equilibrium constant; Rate constant; pH = 7; |
GLUTATHIONE
oxytocin
A
Oxidized glutathione
B
H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2
Conditions | Yield |
---|---|
With potassium chloride In water at 25℃; Equilibrium constant; Rate constant; pH = 7; |
Conditions | Yield |
---|---|
at 80℃; Kinetics; |
Conditions | Yield |
---|---|
In water at 25℃; for 5h; Rate constant; Equilibrium constant; pH 7.0; |
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. |
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. |
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 |
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