Product Name

  • Name

    Heparin

  • EINECS 232-681-7
  • CAS No. 9005-49-6
  • Article Data6
  • CAS DataBase
  • Density 2.13g/cm3
  • Solubility
  • Melting Point 250 °C (decomp)
  • Formula Unspecified
  • Boiling Point 644.9oC at 760mmHg
  • Molecular Weight 1134.93
  • Flash Point 343.8oC
  • Transport Information
  • Appearance white crystalline powder
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 9005-49-6 (Heparin)
  • Hazard Symbols
  • Synonyms Ardeparin;AVE 5026;Centaxarin;CY 222;CY 216;Bemiparin;Arteven;Multiparin;Nadroparin;Nadroparine;Novoheparin;OP 386;OP 622;Octaparin;Pabyrn;Parnaparin;Reviparin;Subeparin;Tinzaparin;Vetren;a-Heparin;LipoHep Forte;KB 101;Heparin sulfate;Hapacarin;H 5284;Fraxiparin;Fragmin A;F 202;Clivarine;Clevarin;Mono-embolex;
  • PSA 652.39000
  • LogP -4.52610

Synthetic route

heparin sodium salt

heparin sodium salt

heparin

heparin

Conditions
ConditionsYield
With Amberlit IR-124 In water at 36.85℃; Equilibrium constant; Kinetics; Further Variations:; Reagents;
C22H34N2O
1333107-97-3

C22H34N2O

heparin

heparin

retinoic acid-heparin conjugate

retinoic acid-heparin conjugate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In formamide; N,N-dimethyl-formamide at 20℃; for 0.0833333h; microfluidics;95.3%
2-aminoethylfolic acid γ-amide
197151-85-2

2-aminoethylfolic acid γ-amide

C22H34N2O
1333107-97-3

C22H34N2O

heparin

heparin

folic acid-heparin-retinoic acid conjugate

folic acid-heparin-retinoic acid conjugate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In formamide; N,N-dimethyl-formamide at 20℃; for 0.0833333h; microfluidics;90.2%
...Expand
Propargylamine
2450-71-7

Propargylamine

heparin

heparin

propargylamine modified heparin

propargylamine modified heparin

Conditions
ConditionsYield
With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 48h; pH=6 - 6.5;78%
heparin

heparin

LMWH; N-deacetylated

LMWH; N-deacetylated

Conditions
ConditionsYield
With hydrazinium sulfate; hydrazine In water at 95℃; for 16h;16%
heparin

heparin

rat serum albumin

rat serum albumin

albumin-heparin conjugate

albumin-heparin conjugate

Conditions
ConditionsYield
With hydrogenchloride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In water at 4℃; for 24h; pH=5.0 - 7.6;
heparin sodium salt

heparin sodium salt

heparin

heparin

Conditions
ConditionsYield
With Amberlit IR-124 In water at 36.85℃; Equilibrium constant; Kinetics; Further Variations:; Reagents;
poly(vinyl amine)

poly(vinyl amine)

hexanal
66-25-1

hexanal

heparin

heparin

poly(N-vinyl hexyl amine-co-N-vinyl heparin amine)

poly(N-vinyl hexyl amine-co-N-vinyl heparin amine)

Conditions
ConditionsYield
sodium cyanoborohydride In methanol; water for 48h;
...Expand
heparin

heparin

O-desulfated heparin

O-desulfated heparin

Conditions
ConditionsYield
Stage #1: heparin With sodium tetrahydroborate In water at 25℃;
Stage #2: With sodium hydroxide pH=13; frozen and lyophilized to dryness;
hyaluronic acid (molecular weight 150.000 Dalton)

hyaluronic acid (molecular weight 150.000 Dalton)

heparin

heparin

heparin-Hy complex

heparin-Hy complex

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfate In water pH=1.48;
poly(lactic acid-co-glycolic acid)

poly(lactic acid-co-glycolic acid)

heparin

heparin

poly(lactide-co-glycolide)

poly(lactide-co-glycolide)

Conditions
ConditionsYield
Stage #1: poly(lactic acid-co-glycolic acid) With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 5h;
Stage #2: heparin In N,N-dimethyl-formamide at 20℃; for 4h;
2,6-Diaminopyridine
141-86-6

2,6-Diaminopyridine

heparin

heparin

2,6-diaminopyridinyl heparin

2,6-diaminopyridinyl heparin

Conditions
ConditionsYield
Stage #1: 2.6-diaminopyridine; heparin In formamide at 50℃; for 6h;
Stage #2: With sodium cyanoborohydride In water; formamide at 50℃; for 24h;
heparin

heparin

C24H38N2O37S6

C24H38N2O37S6

Conditions
ConditionsYield
With heparinase I Enzymatic reaction;
2-aminoethylfolic acid γ-amide
197151-85-2

2-aminoethylfolic acid γ-amide

heparin

heparin

folic acid-heparin conjugate

folic acid-heparin conjugate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In formamide at 20℃; for 48h;
heparin

heparin

A

C12H20O14S
69861-32-1

C12H20O14S

B

C12H20O17S2
69180-27-4

C12H20O17S2

C

C12H20O17S2
119692-05-6

C12H20O17S2

D

C12H20O14S
646502-84-3

C12H20O14S

E

C12H20O14S
71487-52-0

C12H20O14S

F

C12H20O14S
71536-85-1

C12H20O14S

Conditions
ConditionsYield
Stage #1: heparin With hydrazine
Stage #2: With cis-nitrous acid Further stages;
...Expand
Spermine
71-44-3

Spermine

heparin

heparin

heparin (spermine)amide

heparin (spermine)amide

Conditions
ConditionsYield
Stage #1: heparin With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In aq. buffer for 0.166667h; pH=5.54;
Stage #2: Spermine In aq. buffer for 2h; pH=5.54;
iron oxide

iron oxide

heparin

heparin

heparin coated superparamagnetic Fe3O4 nanoparticles

heparin coated superparamagnetic Fe3O4 nanoparticles

Conditions
ConditionsYield
In water for 2h;
heparin

heparin

A

D-Galactose
10257-28-0

D-Galactose

B

2-deoxy-2-amino glucose
90-76-6, 90-77-7, 530-23-4, 579-32-8, 579-33-9, 643-68-5, 2596-19-2, 6490-68-2, 6490-70-6, 6490-72-8, 6490-73-9, 6490-74-0, 14196-84-0, 14196-86-2, 14257-69-3, 58381-21-8

2-deoxy-2-amino glucose

C

D-glucuronic acid
6556-12-3, 489-91-8, 528-16-5, 552-12-5, 577-46-8, 643-33-4, 2240-07-5, 6294-16-2, 10133-02-5, 18402-78-3, 18968-14-4, 21179-08-8, 23018-83-9, 33599-45-0, 33599-46-1, 46171-67-9, 46171-69-1, 46172-26-3, 70021-34-0, 71031-08-8, 104195-06-4, 106499-29-0, 124817-72-7

D-glucuronic acid

D

D-galactosamine
90-76-6, 90-77-7, 530-23-4, 579-32-8, 579-33-9, 643-68-5, 2596-19-2, 6490-68-2, 6490-70-6, 6490-72-8, 6490-73-9, 6490-74-0, 14196-84-0, 14196-86-2, 14257-69-3, 58381-21-8

D-galactosamine

E

C5H10O6

C5H10O6

F

C12H21NO11

C12H21NO11

G

C11H21NO10

C11H21NO10

Conditions
ConditionsYield
With trifluoroacetic acid at 110℃; for 3h;
...Expand
3-aminopropyltriethoxysilane
919-30-2

3-aminopropyltriethoxysilane

heparin

heparin

3-aminopropyltriethoxysilane conjugated heparin

3-aminopropyltriethoxysilane conjugated heparin

Conditions
ConditionsYield
With 4-morpholineethanesulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethanol at 20℃; for 0.666667h;
6(I)-amino-6(I)-deoxycyclomaltoheptaose
29390-67-8

6(I)-amino-6(I)-deoxycyclomaltoheptaose

heparin

heparin

β-cyclodextrin-conjugated heparin

β-cyclodextrin-conjugated heparin

Conditions
ConditionsYield
In water at 20℃; for 24h;
2,2'-dithio-bis[ethylamine]
51-85-4

2,2'-dithio-bis[ethylamine]

heparin

heparin

heparin-cystamine conjugate

heparin-cystamine conjugate

Conditions
ConditionsYield
Stage #1: heparin With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In aq. buffer at 20℃; for 0.333333h; pH=6;
Stage #2: 2,2'-dithio-bis[ethylamine] In aq. buffer for 24h; pH=7; Cooling with ice;
C37H45N3(2+)*2I(1-)

C37H45N3(2+)*2I(1-)

heparin

heparin

heparin and 2-[5-(3,3-dimethyl-1-propyl-2,3-dihydro-1H-indol-2-ylidene)-3-(1-methylpyridin-1-ium-4-yl)penta-1,3-dien-1-yl]-3,3-dimethyl-1-propyl-3H-indol-1-ium diiodide 1:1 complex

heparin and 2-[5-(3,3-dimethyl-1-propyl-2,3-dihydro-1H-indol-2-ylidene)-3-(1-methylpyridin-1-ium-4-yl)penta-1,3-dien-1-yl]-3,3-dimethyl-1-propyl-3H-indol-1-ium diiodide 1:1 complex

Conditions
ConditionsYield
In methanol; aq. phosphate buffer; water pH=7.34;
C37H45N3(2+)*2I(1-)

C37H45N3(2+)*2I(1-)

heparin

heparin

heparin and 2-[5-(3,3-dimethyl-1-propyl-2,3-dihydro-1H-indol-2-ylidene)-3-(1-methylpyridin-1-ium-4-yl)penta-1,3-dien-1-yl]-3,3-dimethyl-1-propyl-3H-indol-1-ium diiodide 2:1 complex

heparin and 2-[5-(3,3-dimethyl-1-propyl-2,3-dihydro-1H-indol-2-ylidene)-3-(1-methylpyridin-1-ium-4-yl)penta-1,3-dien-1-yl]-3,3-dimethyl-1-propyl-3H-indol-1-ium diiodide 2:1 complex

Conditions
ConditionsYield
In methanol; aq. phosphate buffer; water pH=7.34;
C36H42N3(1+)*I(1-)
1609656-27-0

C36H42N3(1+)*I(1-)

heparin

heparin

heparin and 2-[5-(3,3-dimethyl-1-propyl-2,3-dihydro-1H-indol-2-ylidene)-3-(pyridin-4-yl)penta-1,3-dien-1-yl]-3,3-dimethyl-1-propyl-3H-indol-1-ium iodide 1:2 complex

heparin and 2-[5-(3,3-dimethyl-1-propyl-2,3-dihydro-1H-indol-2-ylidene)-3-(pyridin-4-yl)penta-1,3-dien-1-yl]-3,3-dimethyl-1-propyl-3H-indol-1-ium iodide 1:2 complex

Conditions
ConditionsYield
In methanol; aq. phosphate buffer; water pH=7.34;
2-[3-(N-methylpyridin-1-ium-4-yl)-5-(3-propyl-2(3H)-benzothiazolylidene)-1,3-pentadien-1-yl]-3-propylbenzothiazolium iodide

2-[3-(N-methylpyridin-1-ium-4-yl)-5-(3-propyl-2(3H)-benzothiazolylidene)-1,3-pentadien-1-yl]-3-propylbenzothiazolium iodide

heparin

heparin

heparin and 2-[3-(1-methylpyridin-1-ium-4-yl)-5-(3-propyl-2,3-dihydro-1,3-benzothiazol-2-ylidene)penta-1,3-dien-1-yl]-3-propyl-1,3-benzothiazol-3-ium diiodide 1:1 complex

heparin and 2-[3-(1-methylpyridin-1-ium-4-yl)-5-(3-propyl-2,3-dihydro-1,3-benzothiazol-2-ylidene)penta-1,3-dien-1-yl]-3-propyl-1,3-benzothiazol-3-ium diiodide 1:1 complex

Conditions
ConditionsYield
In methanol; aq. phosphate buffer; water pH=7.34;
2-[3-(N-methylpyridin-1-ium-4-yl)-5-(3-propyl-2(3H)-benzothiazolylidene)-1,3-pentadien-1-yl]-3-propylbenzothiazolium iodide

2-[3-(N-methylpyridin-1-ium-4-yl)-5-(3-propyl-2(3H)-benzothiazolylidene)-1,3-pentadien-1-yl]-3-propylbenzothiazolium iodide

heparin

heparin

heparin and 2-[3-(1-methylpyridin-1-ium-4-yl)-5-(3-propyl-2,3-dihydro-1,3-benzothiazol-2-ylidene)penta-1,3-dien-1-yl]-3-propyl-1,3-benzothiazol-3-ium diiodide 1:2 complex

heparin and 2-[3-(1-methylpyridin-1-ium-4-yl)-5-(3-propyl-2,3-dihydro-1,3-benzothiazol-2-ylidene)penta-1,3-dien-1-yl]-3-propyl-1,3-benzothiazol-3-ium diiodide 1:2 complex

Conditions
ConditionsYield
In methanol; aq. phosphate buffer; water pH=7.34;
2-[3-(N-methylpyridin-1-ium-4-yl)-5-(3-propyl-2(3H)-benzothiazolylidene)-1,3-pentadien-1-yl]-3-propylbenzothiazolium iodide

2-[3-(N-methylpyridin-1-ium-4-yl)-5-(3-propyl-2(3H)-benzothiazolylidene)-1,3-pentadien-1-yl]-3-propylbenzothiazolium iodide

heparin

heparin

heparin and 2-[3-(1-methylpyridin-1-ium-4-yl)-5-(3-propyl-2,3-dihydro-1,3-benzothiazol-2-ylidene)penta-1,3-dien-1-yl]-3-propyl-1,3-benzothiazol-3-ium diiodide 1:3 complex

heparin and 2-[3-(1-methylpyridin-1-ium-4-yl)-5-(3-propyl-2,3-dihydro-1,3-benzothiazol-2-ylidene)penta-1,3-dien-1-yl]-3-propyl-1,3-benzothiazol-3-ium diiodide 1:3 complex

Conditions
ConditionsYield
In methanol; aq. phosphate buffer; water pH=7.34;
heparin

heparin

N-desulfated heparin

N-desulfated heparin

Conditions
ConditionsYield
Stage #1: heparin With pyridine In water at 20℃;
Stage #2: With dimethyl sulfoxide In water at 25℃;
heparin

heparin

butan-1-ol
71-36-3

butan-1-ol

A

n-butyl (2-amino-2-deoxy-α-D-glucopyranosyl)-(1→4)-(n-butyl α-L-idopyranosid)uronate

n-butyl (2-amino-2-deoxy-α-D-glucopyranosyl)-(1→4)-(n-butyl α-L-idopyranosid)uronate

B

n-butyl (2-amino-2-deoxy-α-D-glucopyranosyl)-(1→4)-(n-butyl β-D-glucopyranosid)uronate

n-butyl (2-amino-2-deoxy-α-D-glucopyranosyl)-(1→4)-(n-butyl β-D-glucopyranosid)uronate

Conditions
ConditionsYield
With hydrogenchloride; 2,2-dimethoxy-propane In water at 100℃; for 2h;
...Expand

Heparin History

 Heparin (CAS NO.9005-49-6) is discovered in 1916 predates the establishment of the Food and Drug Administration of the United States, although it did not enter clinical trials until 1935.It was originally isolated from canine liver cells, hence its name. Heparin's discovery can be attributed to the research activities of two men, Jay McLean and William Henry Howell.

Heparin Specification

1. Introduction of Heparin
Heparin is one kind of wihte or alomost white powder. The IUPAC name of Heparin is (4S,6R)-6-[(2R,4R)-4,6-Dihydroxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)oxan-3-yl]oxy-3,4-dihydroxy-5-sulfonatooxyoxane-2-carboxylate. The Classification Code of this chemical is Anticoagulants ; Cardiovascular Agents ; Drug / Therapeutic Agent ; Fibrin Modulating Agents ; Fibrinolytic agents ; Hematologic Agents ; Human Data ; Mutation data ; Natural Product ; Reproductive Effect. Heparin can soluble in water.

2. Properties of Heparin
Physical properties about Heparin are:
(1)XLogP3-AA: -10.8; (2)H-Bond Donor: 15; (3)H-Bond Acceptor: 38; (4)Rotatable Bond Count: 21; (5)Tautomer Count: 2; (6)Exact Mass: 1134.006995; (7)MonoIsotopic Mass: 1134.006995; (8)Topological Polar Surface Area: 652; (9)Heavy Atom Count: 70; (10)Formal Charge: 0; (11)Complexity: 2410; (12)Isotope Atom Count: 0; (13)Defined Atom Stereocenter Count: 0; (14)Undefined Atom Stereocenter Count: 20; (15)Defined Bond Stereocenter Count: 0; (16)Undefined Bond Stereocenter Count: 0; (17)Covalently-Bonded Unit Count: 1; (18)Index of Refraction: 1.711; (19)Molar Refractivity: 190.48 cm3; (20)Molar Volume: 486.7 cm3; (21)Surface Tension: 148.8 dyne/cm; (22)Density: 2.13 g/cm3.

3. Structure Descriptors of Heparin
(1)InChI: InChI=1S/C26H42N2O37S5/c1-4(30)27-7-9(31)13(6(56-23(7)39)3-55-67(43,44)45)58-26-19(65-70(52,53)54)12(34)16(20(62-26)22(37)38)60-24-8(28-66(40,41)42)15(63-68(46,47)48)14(5(2-29)57-24)59-25-18(64-69(49,50)51)11(33)10(32)17(61-25)21(35)36/h5-20,23-26,28-29,31-34,39H,2-3H2,1H3,(H,27,30)(H,35,36)(H,37,38)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,
49,50,51)(H,52,53,54)
(2)InChIKey: HTTJABKRGRZYRN-UHFFFAOYSA-N
(3)Canonical SMILES : CC(=O)NC1C(C(C(OC1O)COS(=O)(=O)O)OC2C(C(C(C(O2)C(=O)O)OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)C(=O)O)O)O)OS(=O)(=O)O)OS(=O)(=O)O)NS(=O)(=O)O)O)OS(=O)(=O)O)O

4. Toxicity of Heparin

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 3536units/kg/ (3536units/kg)   Southern Medical Journal. Vol. 80, Pg. 1450, 1987.
man TDLo subcutaneous 1857units/kg/ (1857units/kg)   Southern Medical Journal. Vol. 80, Pg. 1450, 1987.
man TDLo subcutaneous 1857units/kg/ (1857units/kg) CARDIAC: OTHER CHANGES Southern Medical Journal. Vol. 80, Pg. 1450, 1987.
mouse LD50 intraperitoneal 1900mg/kg (1900mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)		 Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 60, Pg. 507, 1964.
mouse LD50 intravenous 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 36, Pg. 1366, 1986.
mouse LD50 subcutaneous 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS		 Arzneimittel-Forschung. Drug Research. Vol. 36, Pg. 1366, 1986.
rat LD50 oral 1950mg/kg (1950mg/kg)   German Offenlegungsschrift Patent Document. Vol. #2636091,
rat LDLo intraperitoneal 420mg/kg (420mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.
women TDLo subcutaneous 30uL/kg/5D-I (.03mL/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Journal of Haematology. Vol. 82, Pg. 620, 1992.
women TDLo subcutaneous 48mg/kg/20D-I (48mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BLOOD: HEMORRHAGE		 Australian and New Zealand Journal of Medicine. Vol. 28, Pg. 59, 1998.
women TDLo subcutaneous 1000units/kg/ (1000units/kg)   Southern Medical Journal. Vol. 80, Pg. 1450, 1987.

5. Safety information of Heparin
S24/25: Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: MI0850000
F: 3-10
Moderately toxic by ingestion, intraperitoneal, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

6. Uses of Heparin
Heparin (CAS NO.9005-49-6) may sometimes be used to treat sports injuries. Heparin, also known as unfractionated heparin, a highly sulfated glycosaminoglycan, is widely used as an injectable anticoagulant, and has the highest negative charge density of any known biological molecule. It can also be used to form an inner anticoagulant surface on various experimental and medical devices such as test tubes and renal dialysis machines.

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