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Basic Information
CAS No.: 24697-74-3
Name: Leonurine hydrochloride
Article Data: 7
Molecular Structure:
Molecular Structure of 24697-74-3 (Leonurine hydrochloride)
Formula: C14H21N3O5
Molecular Weight: 311.338
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;
EINECS: 683-174-6
Density: 1.29 g/cm3
Melting Point: 191-193oC
Boiling Point: 531.6 °C at 760 mmHg
Flash Point: 275.3 °C
Appearance: brown powder
Hazard Symbols: Xi
Risk Codes: 36/37/38
Safety: 26-24/25
PSA: 126.89000
LogP: 2.02040
Synthetic route

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

24697-74-3

Leonurine

Conditions
ConditionsYield
With zinc dibromide In dichloromethane at 20℃;93%

S-methylisothiourea hemisulphate

18780-70-6

Leonuramin

24697-74-3

Leonurine

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

Leonuramin

867-44-7

S-Methylisothiourea sulfate

24697-74-3

Leonurine

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

Leonuramin

322474-21-5

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

A

24697-74-3

Leonurine

B

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%
18780-68-2

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

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
18780-67-1

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

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
530-57-4

3,5-dimethoxy-4-hydroxybenzoic acid

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

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

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

2986-19-8

carbamimidothioic acid methyl ester

24697-74-3

Leonurine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 140℃; for 5h;17 g
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  • pharmaceutical intermediate Leonurine hydrochloride 24697-74-3 CAS NO.24697-74-3 CAS NO.24697-74-3

  • Casno:

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    pharmaceutical intermediate Leonurine hydrochloride 24697-74-3 CAS NO.24697-74-3 CAS NO.24697-74-3

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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;