Product Name

  • Name

    Spermine

  • EINECS 200-754-2
  • CAS No. 71-44-3
  • Article Data27
  • CAS DataBase
  • Density 0.925 g/cm3
  • Solubility 1 M at 20 °C, clear, colorless
  • Melting Point 310-311 °C (dec.)(lit.)
  • Formula C10H26N4
  • Boiling Point 308.4 °C at 760 mmHg
  • Molecular Weight 202.343
  • Flash Point 175.6 °C
  • Transport Information UN 3259 8/PG 2
  • Appearance white to slightly off-white powder crystal
  • Safety 26-36-45-36/37/39-27
  • Risk Codes 36/38-34
  • Molecular Structure Molecular Structure of 71-44-3 (Spermine)
  • Hazard Symbols IrritantXi,CorrosiveC
  • Synonyms 1,4-Butanediamine,N,N'-bis(3-aminopropyl)- (8CI,9CI);Spermine (6CI);1,5,10,14-Tetraazatetradecane;4,9-Diazadodecane-1,12-diamine;Gerontine;Musculamine;N,N'-Bis(3-aminopropyl)-1,4-butanediamine;N,N'-Bis(3-aminopropyl)-1,4-tetramethylenediamine;NSC 268508;Neuridine;
  • PSA 76.10000
  • LogP 1.82580

Synthetic route

3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile
14209-32-6

3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
With sodium; butan-1-ol
With diethyl ether; ammonia; nickel at 140℃; under 250073 Torr; Hydrogenation;
With hydrogenchloride; platinum Hydrogenation;
1,2-bis(1,4,5,6-tetrahydropyrimidin-2-yl)ethane
78706-92-0

1,2-bis(1,4,5,6-tetrahydropyrimidin-2-yl)ethane

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
With sulfuric acid; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane 1.) reflux, 12 h, 2.) xylene, reflux, 3 d; Yield given. Multistep reaction;
kinetin
525-79-1

kinetin

A

N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

B

Spermine
71-44-3

Spermine

C

1,4-diaminobutane
110-60-1

1,4-diaminobutane

Conditions
ConditionsYield
at 30℃; for 24h; effect on poliamine content and ratio in rice embryos of Oryza sativa;
(R)-(-)-abscisic acid
14398-53-9

(R)-(-)-abscisic acid

A

N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

B

Spermine
71-44-3

Spermine

C

1,4-diaminobutane
110-60-1

1,4-diaminobutane

Conditions
ConditionsYield
at 30℃; for 24h; effect on poliamine content and ratio in rice embryos of Oryza sativa;
(-)-Verbaskine
12651-38-6

(-)-Verbaskine

A

Spermine
71-44-3

Spermine

B

(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

Conditions
ConditionsYield
With hydrogenchloride at 150℃; for 18h; sealed tube;
1-(4-Amino-butyl)-tetrahydro-pyrimidin-2-one
73397-39-4

1-(4-Amino-butyl)-tetrahydro-pyrimidin-2-one

acrylonitrile
107-13-1

acrylonitrile

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
Yield given. Multistep reaction;
N'-(4-(N'-hexahydropyrimidyl) butyl)-hexahydro-pyrimidine
77485-28-0

N'-(4-(N'-hexahydropyrimidyl) butyl)-hexahydro-pyrimidine

A

formaldehyd
50-00-0

formaldehyd

B

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
With hydrogenchloride Heating;
1,1'-(butane-1,4-diyl)-2,2'-diphenylbis(hexahydropyrimidine)
185250-13-9

1,1'-(butane-1,4-diyl)-2,2'-diphenylbis(hexahydropyrimidine)

A

Spermine
71-44-3

Spermine

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With hydrogenchloride at 20℃;
1.4-bis-<γ-bromo-propylamino>-butane dihydrobromide

1.4-bis-<γ-bromo-propylamino>-butane dihydrobromide

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
With ethanol; ammonia at 100℃;
1,4-diaminobutane
110-60-1

1,4-diaminobutane

N-<γ-iodo-propyl>-phthalimide

N-<γ-iodo-propyl>-phthalimide

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
at 100℃; anschl. mit wss. KOH, anschl. Erhitzen mit HCl auf 100grad;
N,N'-Bis(3-brompropyl)-1,4-diaminobutan

N,N'-Bis(3-brompropyl)-1,4-diaminobutan

potassium-

potassium-

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
With pentan-1-ol Erwaermen des Reaktionsprodukts mit Hydrazin-hydrat in Aethanol;
(Z)-1-{N-[3-aminopropyl]-N-[4-(3-aminopropyl-ammonio)butyl]-amino}-diazen-1-ium-1,2-diolate

(Z)-1-{N-[3-aminopropyl]-N-[4-(3-aminopropyl-ammonio)butyl]-amino}-diazen-1-ium-1,2-diolate

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
With sodium hydroxide; phosphate buffer at 37℃; pH=5.60 - 8.50; Kinetics; Further Variations:; pH-values;
3,10-dioxo-4,9-diazadodecanediamide
477808-25-6

3,10-dioxo-4,9-diazadodecanediamide

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran for 7h; Heating;
N-[4-(2-methoxycarbonyl-acetylamino)-butyl]-malonamic acid methyl ester
477808-23-4

N-[4-(2-methoxycarbonyl-acetylamino)-butyl]-malonamic acid methyl ester

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3 / methanol / 7 °C
2: BH3*THF / tetrahydrofuran / 7 h / Heating
View Scheme
C24H30N4O4S2
78707-11-6

C24H30N4O4S2

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / sodium methoxide / methanol / 0.33 h / 0 °C
2: 1.) hexamethyldisilazane, fuming sulfuric acid, 2.) diisobutylaluminum hydride / 1.) reflux, 12 h, 2.) xylene, reflux, 3 d
View Scheme
N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2) Ba(OH)2
View Scheme
N-(3-aminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine

N-(3-aminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine

A

N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

B

Spermine
71-44-3

Spermine

C

N-ethyl-1,3-diaminopropane
10563-23-2

N-ethyl-1,3-diaminopropane

D

N1-(3-ethylaminopropyl)butane-1,4-diamine

N1-(3-ethylaminopropyl)butane-1,4-diamine

Conditions
ConditionsYield
With recombinant human polyamine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;
N1-(3-aminopropyl)-N4-(3-(benzylamino)propyl)butane-1,4-diamine

N1-(3-aminopropyl)-N4-(3-(benzylamino)propyl)butane-1,4-diamine

A

N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

B

Spermine
71-44-3

Spermine

C

benzylamine
100-46-9

benzylamine

D

N-{3-[(4-aminobutyl)amino]propyl}(phenylmethyl)amine

N-{3-[(4-aminobutyl)amino]propyl}(phenylmethyl)amine

Conditions
ConditionsYield
With recombinant human polyamine oxidase pH=9.5; Kinetics; pH-value; Reagent/catalyst; Enzymatic reaction;
N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine
1111644-29-1

N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine

A

N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

B

Spermine
71-44-3

Spermine

C

N-ethyl-1,3-diaminopropane
10563-23-2

N-ethyl-1,3-diaminopropane

D

N1-(3-ethylaminopropyl)butane-1,4-diamine

N1-(3-ethylaminopropyl)butane-1,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: spermine oxidase / pH 9.5 / Enzymatic reaction
2: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
1: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction
2: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction
View Scheme
1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride
117654-79-2

1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride

A

N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

B

Spermine
71-44-3

Spermine

C

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction
2: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction
View Scheme
N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

C15H25N6O3S(1+)

C15H25N6O3S(1+)

A

Spermine
71-44-3

Spermine

B

5'-methylthioadenosine

5'-methylthioadenosine

Conditions
ConditionsYield
With Thermus thermophilus triamine/agmatine aminopropyltransferase; diothiothreitol at 37℃; pH=9; Kinetics; aq. buffer; Enzymatic reaction;
3,3′,3″,3′″-(butane-1,4-diylbis(azanetriyl))tetrapropanenitrile

3,3′,3″,3′″-(butane-1,4-diylbis(azanetriyl))tetrapropanenitrile

A

Spermine
71-44-3

Spermine

B

N,N,N',N'-tetra(3-aminopropyl)-1,4-butanediamine
120239-63-6

N,N,N',N'-tetra(3-aminopropyl)-1,4-butanediamine

C

N,N,N'-tris(3-aminopropyl)-1,4-butanediamine

N,N,N'-tris(3-aminopropyl)-1,4-butanediamine

Conditions
ConditionsYield
With ammonia; hydrogen In tetrahydrofuran at 50℃; under 33753.4 Torr; Autoclave;
C32H48N6O12S2

C32H48N6O12S2

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: thionyl chloride; methanol / 2 h / 0 - 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine; dmap / N,N-dimethyl-formamide / 24 h / 20 °C
2.2: 24 h / 0 - 20 °C / Inert atmosphere
View Scheme
C22H32N6O8S2

C22H32N6O8S2

Spermine
71-44-3

Spermine

Conditions
ConditionsYield
Stage #1: C22H32N6O8S2 With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol In N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;
Stage #3: With trifluoroacetic acid In dichloromethane
30 mg
Spermine
71-44-3

Spermine

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

1,12-diphthalimido-4,9-diazadodecane
104435-59-8

1,12-diphthalimido-4,9-diazadodecane

Conditions
ConditionsYield
In chloroform at 20℃; for 1h;100%
In dichloromethane Ambient temperature;86%
In chloroform Ambient temperature;70%
Spermine
71-44-3

Spermine

3-(4'-acetoxyphenyl)propionyl chloride
63867-00-5

3-(4'-acetoxyphenyl)propionyl chloride

N1,N5,N10,N14-tertakis[3-(4-acetoxyphenyl)propanoyl]-1,5,10,14-tetraazatetradecane

N1,N5,N10,N14-tertakis[3-(4-acetoxyphenyl)propanoyl]-1,5,10,14-tetraazatetradecane

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;100%
3-indolylglyoxylic acid
1477-49-2

3-indolylglyoxylic acid

Spermine
71-44-3

Spermine

trifluoroacetic acid
76-05-1

trifluoroacetic acid

N1,N4-bis(3-(2-(1H-indol-3-yl)-2-oxoacetamido)propyl)butane-1,4-diaminium 2,2,2-trifluoroacetate

N1,N4-bis(3-(2-(1H-indol-3-yl)-2-oxoacetamido)propyl)butane-1,4-diaminium 2,2,2-trifluoroacetate

Conditions
ConditionsYield
Stage #1: 3-indolylglyoxylic acid; Spermine With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 23h; Inert atmosphere;
Stage #2: trifluoroacetic acid In methanol; water
100%
Spermine
71-44-3

Spermine

tolfenamic Acid
13710-19-5

tolfenamic Acid

tolfenamic acid spermine salt

tolfenamic acid spermine salt

Conditions
ConditionsYield
In methanol at 20℃; for 0.5h;99%
Spermine
71-44-3

Spermine

C10H26N6O2

C10H26N6O2

Conditions
ConditionsYield
With nitrogen(II) oxide In acetonitrile under 3800 Torr; for 20h; Ambient temperature;98%
Spermine
71-44-3

Spermine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

N1,N12-di(trifluoroacetyl)-1,12-diamino-4,9-diazadodecane
168788-09-8

N1,N12-di(trifluoroacetyl)-1,12-diamino-4,9-diazadodecane

Conditions
ConditionsYield
With water In methanol Heating;98%
In water; acetonitrile at 100℃;95%
In water; acetonitrile94%
Spermine
71-44-3

Spermine

(E)-3-(4-hydroxyphenyl)-2-methyl-2-propenoyl chloride
402598-52-1

(E)-3-(4-hydroxyphenyl)-2-methyl-2-propenoyl chloride

N1,N5,N10,N14-tertakis[3-(4-acetoxyphenyl)-2-methyl-2-propenoyl]-1,5,10,14-tetraazatetradecane
402598-61-2

N1,N5,N10,N14-tertakis[3-(4-acetoxyphenyl)-2-methyl-2-propenoyl]-1,5,10,14-tetraazatetradecane

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;98%
Spermine
71-44-3

Spermine

allyl phenyl carbonate
16308-68-2

allyl phenyl carbonate

N1,N8-bis(allyloxycarbonyl)spermine

N1,N8-bis(allyloxycarbonyl)spermine

Conditions
ConditionsYield
In dichloromethane at 20℃;98%
Spermine
71-44-3

Spermine

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

spermine fumarate

spermine fumarate

Conditions
ConditionsYield
In water for 0.25h;98%
Spermine
71-44-3

Spermine

9-(5-O-dimethoxytrityl-2-deoxy-β-D-erythro-pentofuranose)-6-(1,2,4-triazol-4-yl)purine
244639-79-0

9-(5-O-dimethoxytrityl-2-deoxy-β-D-erythro-pentofuranose)-6-(1,2,4-triazol-4-yl)purine

5'-O-dimethoxytrityl-6-N-(4,9,13-triazatridecane-1-yl)-2'-deoxyadenosine
259141-08-7

5'-O-dimethoxytrityl-6-N-(4,9,13-triazatridecane-1-yl)-2'-deoxyadenosine

Conditions
ConditionsYield
With pyridine at 70℃; for 8h; Substitution;97%
In pyridine at 70℃; Substitution;
Spermine
71-44-3

Spermine

succinimidyl (E)-3-(trioxsalen-4'-yl)propenoate
1114539-81-9

succinimidyl (E)-3-(trioxsalen-4'-yl)propenoate

N1,N12-bis[(E)-3-(trioxsalen-4'-yl)propenoyl]spermine bishydroxysuccinimidate salt

N1,N12-bis[(E)-3-(trioxsalen-4'-yl)propenoyl]spermine bishydroxysuccinimidate salt

Conditions
ConditionsYield
In dichloromethane at 25℃; for 1h;96%
formaldehyd
50-00-0

formaldehyd

Spermine
71-44-3

Spermine

N'-(4-(N'-hexahydropyrimidyl) butyl)-hexahydro-pyrimidine
77485-28-0

N'-(4-(N'-hexahydropyrimidyl) butyl)-hexahydro-pyrimidine

Conditions
ConditionsYield
In water at 0℃; for 0.833333h;95%
In water at 20℃; for 20h;
Spermine
71-44-3

Spermine

benzaldehyde
100-52-7

benzaldehyde

1,1'-(butane-1,4-diyl)-2,2'-diphenylbis(hexahydropyrimidine)
185250-13-9

1,1'-(butane-1,4-diyl)-2,2'-diphenylbis(hexahydropyrimidine)

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at -78 - 23℃;95%
In benzene Heating;
Spermine
71-44-3

Spermine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1-trifluoroacetyl-5,10,14-tris-Boc-spermine
201984-66-9

1-trifluoroacetyl-5,10,14-tris-Boc-spermine

Conditions
ConditionsYield
Stage #1: Spermine; ethyl trifluoroacetate, In methanol at -78 - 0℃; for 1h;
Stage #2: di-tert-butyl dicarbonate In methanol at 0 - 25℃; for 15h;
95%
Stage #1: Spermine; ethyl trifluoroacetate, In methanol at -78 - 4℃; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In methanol at 4℃; Inert atmosphere;
82.9%
Stage #1: Spermine; ethyl trifluoroacetate, In methanol at -78℃; for 1h; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In methanol at 0 - 25℃; for 24h; Inert atmosphere;
49%
1) MeOH, 78 deg C, 1 h then 0 deg C, 1 h, 2) MeOH, 0 to 25 deg C, 1 h; Multistep reaction;
Stage #1: Spermine; ethyl trifluoroacetate, In methanol at -78 - 0℃; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In methanol at 0 - 20℃; for 18h; Inert atmosphere;
Spermine
71-44-3

Spermine

dihydrocholesterone
566-88-1

dihydrocholesterone

3β-(12-amino-4,9-diaza-dodecyl)amino-cholestane
177745-14-1

3β-(12-amino-4,9-diaza-dodecyl)amino-cholestane

Conditions
ConditionsYield
Stage #1: Spermine; dihydrocholesterone With titanium(IV) isopropylate In methanol at 20℃; for 12h;
Stage #2: With sodium tetrahydroborate In methanol at -78℃; for 2h; Further stages.;
95%
Spermine
71-44-3

Spermine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

N1,N14-bis(trifluoroacetyl)spermine ditrifluoroacetate

N1,N14-bis(trifluoroacetyl)spermine ditrifluoroacetate

Conditions
ConditionsYield
In water; acetonitrile Heating;94%
With water In acetonitrile Heating;93%
In acetonitrile Reflux;93%
With water In acetonitrile Reflux;93%
With water In acetonitrile Reflux;
Spermine
71-44-3

Spermine

5-benzoyl-3-(cyclopent-1-en-1-yl)-5-phenyl-1,5-dihydro-4H-pyrazol-4-one

5-benzoyl-3-(cyclopent-1-en-1-yl)-5-phenyl-1,5-dihydro-4H-pyrazol-4-one

C17H30N4O
220221-33-0

C17H30N4O

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h; regioselective reaction;93%
Spermine
71-44-3

Spermine

trifluoroacetic acid
76-05-1

trifluoroacetic acid

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

N1,N4-bis(3-(3-phenylpropanamido)propyl)butane-1,4-diaminium 2,2,2-trifluoroacetate

N1,N4-bis(3-(3-phenylpropanamido)propyl)butane-1,4-diaminium 2,2,2-trifluoroacetate

Conditions
ConditionsYield
Stage #1: Spermine; 3-Phenylpropionic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 23h; Inert atmosphere;
Stage #2: trifluoroacetic acid In N,N-dimethyl-formamide Inert atmosphere;
92%
benzoyl cyanide
613-90-1

benzoyl cyanide

Spermine
71-44-3

Spermine

N1,N12-dibenzoylspermine
111574-87-9

N1,N12-dibenzoylspermine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h;91%
In dichloromethane for 15h; Ambient temperature;91%
In dichloromethane Ambient temperature;91%
Spermine
71-44-3

Spermine

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

C,C,C-Trifluoro-N-(3-trifluoromethanesulfonylamino-propyl)-N-{4-[trifluoromethanesulfonyl-(3-trifluoromethanesulfonylamino-propyl)-amino]-butyl}-methanesulfonamide
144534-70-3

C,C,C-Trifluoro-N-(3-trifluoromethanesulfonylamino-propyl)-N-{4-[trifluoromethanesulfonyl-(3-trifluoromethanesulfonylamino-propyl)-amino]-butyl}-methanesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h; Ambient temperature; -30 deg C up to r.t.;90%
Spermine
71-44-3

Spermine

N2-benzyloxycarbonyl-N6-t-butoxycarbonyl-L-lysine 4-nitrophenyl ester
2212-69-3

N2-benzyloxycarbonyl-N6-t-butoxycarbonyl-L-lysine 4-nitrophenyl ester

((S)-5-{3-[4-(3-Amino-propylamino)-butylamino]-propylcarbamoyl}-5-benzyloxycarbonylamino-pentyl)-carbamic acid tert-butyl ester
199340-70-0

((S)-5-{3-[4-(3-Amino-propylamino)-butylamino]-propylcarbamoyl}-5-benzyloxycarbonylamino-pentyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 2.5h; Ambient temperature;90%
2,2-diphenyl-benzo[1,3]dioxole-4-carbonyl chloride
54888-42-5

2,2-diphenyl-benzo[1,3]dioxole-4-carbonyl chloride

Spermine
71-44-3

Spermine

C90H74N4O12

C90H74N4O12

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 50℃;90%
Spermine
71-44-3

Spermine

8-bromocaffeine
10381-82-5

8-bromocaffeine

8-(3-(4-(3-aminopropylamino)butylamino)propylamino)caffeine

8-(3-(4-(3-aminopropylamino)butylamino)propylamino)caffeine

Conditions
ConditionsYield
In ethanol for 40h; Reflux;90%
In ethanol
Spermine
71-44-3

Spermine

(E)-3-(4-Nitro-phenyl)-acrylic acid 2,5-dioxo-pyrrolidin-1-yl ester
125802-80-4

(E)-3-(4-Nitro-phenyl)-acrylic acid 2,5-dioxo-pyrrolidin-1-yl ester

(E)-3-(4-Nitro-phenyl)-N-[3-(4-{3-[(E)-3-(4-nitro-phenyl)-acryloylamino]-propylamino}-butylamino)-propyl]-acrylamide

(E)-3-(4-Nitro-phenyl)-N-[3-(4-{3-[(E)-3-(4-nitro-phenyl)-acryloylamino]-propylamino}-butylamino)-propyl]-acrylamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;89%
Spermine
71-44-3

Spermine

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

C54H82N4O4

C54H82N4O4

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane88%
Spermine
71-44-3

Spermine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

2,2,2-trifluoro-N-(3-{4-[3-(2,2,2-trifluoro-acetylamino)-propylamino]-butylamino}-propyl)-acetamide trifluoroacetate

2,2,2-trifluoro-N-(3-{4-[3-(2,2,2-trifluoro-acetylamino)-propylamino]-butylamino}-propyl)-acetamide trifluoroacetate

Conditions
ConditionsYield
With water In acetonitrile for 18h; Heating / reflux;88%
Spermine
71-44-3

Spermine

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

N-(12-phthalimido-4,9-diazadodecyl)phthalimide*2HCl

N-(12-phthalimido-4,9-diazadodecyl)phthalimide*2HCl

Conditions
ConditionsYield
In tetrahydrofuran at 23℃; for 2h;87%
Spermine
71-44-3

Spermine

(E)-3,4-di-O-acetylcaffeoyl chloride
82592-68-5, 98631-72-2

(E)-3,4-di-O-acetylcaffeoyl chloride

N1,N5,N10,N14-tertakis[3-(3,4-diacetoxyphenyl)-2-propenoyl]-1,5,10,14-tetraazatetradecane

N1,N5,N10,N14-tertakis[3-(3,4-diacetoxyphenyl)-2-propenoyl]-1,5,10,14-tetraazatetradecane

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;87%
Spermine
71-44-3

Spermine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

di-tert-butyl butane-1,4-diylbis((3-aminopropyl)carbamate)
177213-61-5

di-tert-butyl butane-1,4-diylbis((3-aminopropyl)carbamate)

Conditions
ConditionsYield
Stage #1: Spermine With ethyl trifluoroacetate, In methanol at 0℃; for 0.5h;
Stage #2: di-tert-butyl dicarbonate In methanol at 20℃;
Stage #3: With sodium hydroxide In methanol at 20℃; for 4h;
87%
Stage #1: Spermine With ethyl trifluoroacetate, In methanol at -78℃; for 16h;
Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 12h;
Stage #3: With sodium hydroxide In methanol at 20℃; for 12h;
Spermine
71-44-3

Spermine

C10H22Cl2N7P3

C10H22Cl2N7P3

Conditions
ConditionsYield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In chloroform for 48h; Ambient temperature;86.3%
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In chloroform at 20℃; Inert atmosphere;
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In chloroform at 20℃; Inert atmosphere;

Spermine Chemical Properties

Product Name: Diaminopropyltetramethylenediamine (CAS NO.71-44-3)

Empirical Formula: C10H26N4
Molecular Weight: 202.3402 
EINECS: 206-189-8
Melting point: 310-311 °C (dec.)(lit.)
Appearance: Clear colorless liquid
Storage temp.: 2-8°C
Solubility: H2O: 1 M at 20 °C, clear, colorless
Form: Powder
Sensitive: Air Sensitive & Hygroscopic
Stable: Stable. Reacts with water.
Index of Refraction: 1.484
Density: 0.925 g/cm3
Flash Point: 175.6 °C
Enthalpy of Vaporization: 54.91 kJ/mol
Boiling Point: 308.4 °C at 760 mmHg
Vapour Pressure: 0.000683 mmHg at 25 °C
Surface Tension: 38.3 dyne/cm
Index of Refraction: 1.484 
Molar Refractivity: 62.63 cm3 
Molar Volume: 218.5 cm3 
XLogP3-AA: -1.1
H-Bond Donor: 4
H-Bond Acceptor: 4
Structure Descriptors of Diaminopropyltetramethylenediamine (CAS NO.71-44-3):
  IUPAC Name: N,N'-bis(3-aminopropyl)butane-1,4-diamine
  Canonical SMILES: C(CCNCCCN)CNCCCN
  InChI: InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2 
  InChIKey: PFNFFQXMRSDOHW-UHFFFAOYSA-N          
Product Categories: Aliphatics; Amines

Spermine Uses

 Diaminopropyltetramethylenediamine (CAS NO.71-44-3) can be used as an organic phosphorus pesticide intermediats. At the same time, it is a typical anionic surfactant with good penetration, emulsification, foam and decontamination capabilities, so it is widely used in chemical, pesticide, fiber, electric crossing, mineral and other industries, especiallily for cosmetics, toothpaste, shampoo and other manufacturings. In the textile industry, it is used for washing wool and silk.

Spermine Production

Take coconut oil as the raw material and then with Sulfuric acid by sulfonation to get: Diaminopropyltetramethylenediamine (CAS NO.71-44-3).

Spermine Toxicity Data With Reference

1.    

mmo-sat 100 µmol/L

    AMACCQ    Antimicrobial Agents and Chemotherapy. 9 (1976),77.
2.    

cyt-hmn:hla 2 mmol/L

    JCLLAX    Journal of Cellular Physiology. 78 (1971),217.
3.    

dni-rat:lvr 100 µmol/L

    BIJOAK    Biochemical Journal. 146 (1975),697.
4.    

ipr-rat LD50:33 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 88 (1987),433.
5.    

ivn-rat LD50:65 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 165 (1967),374.
6.    

orl-mus LD30:650 mg/kg

    AGACBH    Agents and Actions, A Swiss Journal of Pharmacology. 14 (1984),228.
7.    

ipr-mus LDLo:8 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 23 (1972),288.
8.    

scu-mus LD30:280 mg/kg

    AGACBH    Agents and Actions, A Swiss Journal of Pharmacology. 14 (1984),228.
9.    

ivn-mus LD50:56 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00641 .

Spermine Consensus Reports

Reported in EPA TSCA Inventory.

Spermine Safety Profile

Poison by intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by ingestion. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.
Safety Information of Diaminopropyltetramethylenediamine (CAS NO.71-44-3):
Hazard Codes: IrritantXi,CorrosiveC
Risk Statements: 36/38-34 
R34:Causes burns. 
R36/38:Irritating to eyes and skin.
Safety Statements: 26-36-45-36/37/39-27 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S27:Take off immediately all contaminated clothing. 
S36:Wear suitable protective clothing. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Spermine Specification

 Diaminopropyltetramethylenediamine , its cas register number is 71-44-3. It also can be called N,N'-Bis(3-aminopropyl)-1,4-butandiamin ; N,N'-Bis(3-aminopropyl)tetramethylenediamine ; 4,9-Diazadodecamethylenediamine ; and 1,4-Butanediamine, N1,N4-bis(3-aminopropyl)- .

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