• Name

  Sanshool

• EINECS
• CAS No. 504-97-2
• Article Data3
• CAS DataBase
• Density 0.904 g/cm³
• Solubility
• Melting Point 63-65 °C
• Formula C₁₆H₂₅NO
• Boiling Point 423.5 °C at 760 mmHg
• Molecular Weight 247.381
• Flash Point 259.3 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 2,6,8,10-Dodecatetraenamide,N-(2-methylpropyl)-, (E,E,Z,E)-;2,6,8,10-Dodecatetraenamide, N-isobutyl-,(E,E,Z,E)- (8CI);2E,6Z,8E,10E-Dodecatetraenoic acid N-(2-methylpropyl)amide;Echinacein;Echinaceine;N-(2-Methylpropyl)-2E,6Z,8E,10E-dodecatetraenamide;N-Isobutyl-trans-2,cis-6,trans-8,trans-10-dodecatetraenamide;Neoherculin;Neoherculine;Sanshool;a-Sanshooel;a-Sanshool;
• PSA 32.59000
• LogP 4.62380

Synthetic route

(2E,8E,10E)-N-isobutyldodeca-2,8,10-trien-6-yneamide

504-97-2

Alpha-Sanshool

Conditions

Conditions	Yield
With copper diacetate; silver nitrate; zinc In methanol; water for 24h;	53%

18744-21-3

2E,6Z,8E,10E-dodecatetraenoic acid

78-81-9

isobutylamine

504-97-2

Alpha-Sanshool

Conditions

Conditions	Yield
(i) (COCl)2, (ii) /BRN= 385626/, Et3N; Multistep reaction;

142-83-6

trans,trans-2,4-Hexadienal

98095-55-7

(E)-6-(Triphenyl-λ5-phosphanylidene)-hex-2-enoic acid isobutyl-amide

A

504-97-2

Alpha-Sanshool

B

10076-00-3

Beta-Sanshool

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; dimethyl sulfoxide at 0℃; Yield given. Yields of byproduct given;

...Expand

142-83-6

trans,trans-2,4-Hexadienal

504-97-2

Alpha-Sanshool

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOEt, NaI 2: KOH 4: (i) (COCl)2, (ii) /BRN= 385626/, Et3N View Scheme

18744-20-2

Decatrien-(4cis.6trans.8trans)-saeure

504-97-2

Alpha-Sanshool

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: (i) (COCl)2, (ii) /BRN= 385626/, Et3N View Scheme

18744-19-9

Decatrien-(4cis.6trans.8trans)-saeureethylester

504-97-2

Alpha-Sanshool

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: KOH 3: (i) (COCl)2, (ii) /BRN= 385626/, Et3N View Scheme

140677-99-2, 141943-16-0, 140677-83-4

hept-2-en-6-ynoic acid methyl ester

504-97-2

Alpha-Sanshool

Conditions

Conditions

Yield

Multi-step reaction with 5 steps 1: sodium hydroxide / tetrahydrofuran / 1 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; diethyl cyanophosphonate / tetrahydrofuran / 1.5 h / 0 - 20 °C 3: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C 4: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran / 2 h / 50 °C 5: silver nitrate; zinc; copper diacetate / water; methanol / 24 h View Scheme

101861-38-5, 121318-58-9

(E)-hept-2-en-6-ynoic acid

504-97-2

Alpha-Sanshool

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine; diethyl cyanophosphonate / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran / 2 h / 50 °C 4: silver nitrate; zinc; copper diacetate / water; methanol / 24 h View Scheme

138691-20-0

(E)-N-(2-methylpropyl)-2-hepten-6-ynamide

504-97-2

Alpha-Sanshool

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran / 2 h / 50 °C 3: silver nitrate; zinc; copper diacetate / water; methanol / 24 h View Scheme

108-31-6

maleic anhydride

504-97-2

Alpha-Sanshool

102461-89-2

(+/-)-3c-(6t-isobutylcarbamoyl-hexa-1,5-dien-c-yl)-6c-methyl-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride

Conditions

Conditions	Yield
With benzene

504-97-2

Alpha-Sanshool

10076-00-3

Beta-Sanshool

Conditions

Conditions	Yield
With iodine; Petroleum ether Irradiation.mit Gluehlampenlicht;
With hexane; iodine Irradiation.mit Gluehlampenlicht;
With iodine
With iodine In hexane for 1h; Irradiation;	190 mg

60-29-7

diethyl ether

504-97-2

Alpha-Sanshool

palladium

palladium

68125-01-9

N-(2-methylpropyl)dodecanamide

Conditions

Conditions	Yield
Hydrogenation;

...Expand

504-97-2

Alpha-Sanshool

64-19-7

acetic acid

palladium

palladium

68125-01-9

N-(2-methylpropyl)dodecanamide

Conditions

Conditions	Yield
Hydrogenation;

...Expand

2,6,8,10-Dodecatetraenamide,N-(2-methylpropyl)-, (2E,6Z,8E,10E)- Specification