Product Name

  • Name

    Leonurine hydrochloride

  • EINECS 683-174-6
  • CAS No. 24697-74-3
  • Article Data7
  • CAS DataBase
  • Density 1.29 g/cm3
  • Solubility
  • Melting Point 191-193oC
  • Formula C14H21N3O5
  • Boiling Point 531.6 °C at 760 mmHg
  • Molecular Weight 311.338
  • Flash Point 275.3 °C
  • Transport Information
  • Appearance brown powder
  • Safety 26-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 24697-74-3 (Leonurine hydrochloride)
  • Hazard Symbols Xi
  • Synonyms Leonurine;Benzoicacid, 4-hydroxy-3,5-dimethoxy-, ester with (4-hydroxybutyl)guanidine (8CI);Leonurine (7CI);Guanidine, (4-hydroxybutyl)-, 4-hydroxy-3,5-dimethoxybenzoate(8CI);Guanidine, (4-hydroxybutyl)-, 4-hydroxy-3,5-dimethoxybenzoate (ester)(8CI);4-Guanidino-1-butanol syringate;4-Hydroxy-3,5-dimethoxybenzoic acid d-guanidinobutyl ester;Leonurin;Syringic acid d-guanidinobutylester;[4-(4-Hydroxy-3,5-dimethoxybenzoyloxy)butyl]guanidine;
  • PSA 126.89000
  • LogP 2.02040

Synthetic route

4-(2,3-bis(tert-butoxycarbonyl)guanidino)butyl 4-hydroxy-3,5-dimethoxybenzoate

4-(2,3-bis(tert-butoxycarbonyl)guanidino)butyl 4-hydroxy-3,5-dimethoxybenzoate

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
With zinc dibromide In dichloromethane at 20℃;93%
S-methylisothiourea hemisulphate

S-methylisothiourea hemisulphate

Leonuramin
18780-70-6

Leonuramin

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 120℃; for 6h;65%
Leonuramin
18780-70-6

Leonuramin

S-Methylisothiourea sulfate
867-44-7

S-Methylisothiourea sulfate

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 120℃; for 6h;65%
Leonuramin
18780-70-6

Leonuramin

N,N'-bis-Boc-S-methyl-isothiourea
322474-21-5

N,N'-bis-Boc-S-methyl-isothiourea

A

Leonurine
24697-74-3

Leonurine

B

3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester
1260119-24-1

3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃;A 30%
B 5%
...Expand
4-ethoxycarbonyloxy-3,5-dimethoxy-benzoyl chloride
18780-68-2

4-ethoxycarbonyloxy-3,5-dimethoxy-benzoyl chloride

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; dmap / dichloromethane / 6 h / 0 - 20 °C
2.1: ammonium hydroxide / methanol / 4 h / 20 °C
2.2: Raney nickel / 10 h / 20 °C
3.1: water; N,N-dimethyl-formamide / 6 h / 120 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine; dmap / dichloromethane / 0 - 20 °C
2: ammonium hydroxide / methanol / 20 °C
3: hydrogen / methanol / 10 h / 25 °C / 760.05 Torr
4: N,N-dimethyl-formamide; water / 6 h / 120 °C
View Scheme
4-[(ethoxycarbonyl)oxy]-3,5-dimethoxybenzoic acid
18780-67-1

4-[(ethoxycarbonyl)oxy]-3,5-dimethoxybenzoic acid

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: thionyl chloride / 1 h / Reflux
2.1: triethylamine; dmap / dichloromethane / 6 h / 0 - 20 °C
3.1: ammonium hydroxide / methanol / 4 h / 20 °C
3.2: Raney nickel / 10 h / 20 °C
4.1: water; N,N-dimethyl-formamide / 6 h / 120 °C
View Scheme
Multi-step reaction with 5 steps
1: thionyl chloride / Reflux
2: triethylamine; dmap / dichloromethane / 0 - 20 °C
3: ammonium hydroxide / methanol / 20 °C
4: hydrogen / methanol / 10 h / 25 °C / 760.05 Torr
5: N,N-dimethyl-formamide; water / 6 h / 120 °C
View Scheme
3,5-dimethoxy-4-hydroxybenzoic acid
530-57-4

3,5-dimethoxy-4-hydroxybenzoic acid

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium hydroxide / 6 h / Cooling
2: thionyl chloride / Reflux
3: triethylamine; dmap / dichloromethane / 0 - 20 °C
4: ammonium hydroxide / methanol / 20 °C
5: hydrogen / methanol / 10 h / 25 °C / 760.05 Torr
6: N,N-dimethyl-formamide; water / 6 h / 120 °C
View Scheme
Multi-step reaction with 5 steps
1.1: dmap / dichloromethane / 20 h
2.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 1 h / 20 °C
2.2: 6 h / 20 °C
3.1: trifluoromethylsulfonic anhydride; triethylamine / dichloromethane / 6 h
4.1: acetic acid; zinc / 2 h
5.1: N,N-dimethyl-formamide / 5 h / 140 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 5 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C
3: sodium hydroxide / methanol / 20 °C
4: zinc dibromide / dichloromethane / 20 °C
View Scheme
C17H23NO8

C17H23NO8

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium hydroxide / methanol / 20 °C
2: hydrogen / methanol / 10 h / 25 °C / 760.05 Torr
3: N,N-dimethyl-formamide; water / 6 h / 120 °C
View Scheme
C15H19NO7

C15H19NO7

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoromethylsulfonic anhydride; triethylamine / dichloromethane / 6 h
2: acetic acid; zinc / 2 h
3: N,N-dimethyl-formamide / 5 h / 140 °C
View Scheme
C15H21NO6

C15H21NO6

carbamimidothioic acid methyl ester
2986-19-8

carbamimidothioic acid methyl ester

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 140℃; for 5h;17 g
O-acetylsyringic acid
6318-20-3

O-acetylsyringic acid

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 1 h / 20 °C
1.2: 6 h / 20 °C
2.1: trifluoromethylsulfonic anhydride; triethylamine / dichloromethane / 6 h
3.1: acetic acid; zinc / 2 h
4.1: N,N-dimethyl-formamide / 5 h / 140 °C
View Scheme
Multi-step reaction with 3 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C
2: sodium hydroxide / methanol / 20 °C
3: zinc dibromide / dichloromethane / 20 °C
View Scheme
4-(2,3-bis(tert-butoxycarbonyl)guanidino)butyl-4-acetoxy-3,5-dimethoxybenzoate

4-(2,3-bis(tert-butoxycarbonyl)guanidino)butyl-4-acetoxy-3,5-dimethoxybenzoate

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / methanol / 20 °C
2: zinc dibromide / dichloromethane / 20 °C
View Scheme
C15H29N3O5

C15H29N3O5

Leonurine
24697-74-3

Leonurine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C
2: sodium hydroxide / methanol / 20 °C
3: zinc dibromide / dichloromethane / 20 °C
View Scheme
Leonurine
24697-74-3

Leonurine

UDP-glucuronic acid
2616-64-0

UDP-glucuronic acid

A

leonurine-O-glucuronide

leonurine-O-glucuronide

B

C13H19N3O5

C13H19N3O5

Conditions
ConditionsYield
With recombinant human UDP-glucuronosyltransferase UGT1A1; NADPH; magnesium chloride In aq. phosphate buffer at 37℃; for 1h; pH=7.4; Catalytic behavior; Kinetics; Reagent/catalyst; Concentration; Enzymatic reaction;
...Expand

Leonurine hydrochloride Specification

Leonurine hydrochloride(CAS NO.24697-74-3) is one of the chemical constituents of the South African plant Leonotis leonurus.  IT is also called 4-hydroxy-3,5-dimethoxybenzoic acid d-guanidinobutyl ester; syringic acid d-guanidinobutyl ester; [4-(4-hydroxy-3,5-dimethoxybenzoyloxy)butyl]guanidine; 4-guanidino-1-butanol syringate. It is a mildly psychoactive alkaloid found in species Leonotis nepetifolia, Leonotis artemisia as well as other plants of family Lamiaceae. Leonurine hydrochloride is easily extracted into water, as well as from the essential oil of Leonurus sibiricus.

Physical properties about Leonurine hydrochloride are: (1)ACD/LogP: 2.503; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 0.50; (4)ACD/LogD (pH 7.4): 0.47; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 5.47; (8)ACD/KOC (pH 7.4): 5.01; (9)#H bond acceptors: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.554; (13)Molar Refractivity: 76.902 cm3; (14)Molar Volume: 240.086 cm3; (15)Polarizability: 30.486 10-24cm3; (16)Surface Tension: 46.8089981079102 dyne/cm; (17)Density: 1.297 g/cm3; (18)Flash Point: 275.311 °C; (19)Enthalpy of Vaporization: 83.749 kJ/mol; (20)Boiling Point: 531.615 °C at 760 mmHg

Uses of Leonurine hydrochloride: Leonurine hydrochloride is used with blood stasis, swelling of the role of diuresis, it is a traditional healer. It can be inhibit platelet aggregation, prevent thrombosis; it also be used as peripheral vascular dilatation and reduce vascular resistance. At the last it can be certain antihypertensive.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17);
(2)InChIKey=WNGSUWLDMZFYNZ-UHFFFAOYSA-N;
(3)SmilesC(c1cc(c(c(c1)OC)O)OC)(=O)OCCCCNC(=N)N;

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