504-97-2

Usage

Uses

Used in Culinary Industry:
Sanshool is used as a flavor enhancer for its unique tingling and numbing sensation, which can enhance the overall sensory experience of food.
Used in Pharmaceutical Industry:
Sanshool is used as a potential natural pain reliever due to its potential medicinal properties.
Used in Research:
Sanshool is used as a subject of study for its unique sensory effects and potential applications in various fields, such as food science and medicine.

InChI:InChI=1/C16H25NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h4-9,12-13,15H,10-11,14H2,1-3H3,(H,17,18)/b5-4+,7-6+,9-8-,13-12+

Synthetic route

(2E,8E,10E)-N-isobutyldodeca-2,8,10-trien-6-yneamide → Alpha-Sanshool (504-97-2)

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

2E,6Z,8E,10E-dodecatetraenoic acid (18744-21-3) + isobutylamine (78-81-9) → Alpha-Sanshool (504-97-2)

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

trans,trans-2,4-Hexadienal (142-83-6) + (E)-6-(Triphenyl-λ5-phosphanylidene)-hex-2-enoic acid isobutyl-amide (98095-55-7) → Alpha-Sanshool (504-97-2) + Beta-Sanshool (10076-00-3)

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

trans,trans-2,4-Hexadienal (142-83-6) → Alpha-Sanshool (504-97-2)

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

Decatrien-(4cis.6trans.8trans)-saeure (18744-20-2) → Alpha-Sanshool (504-97-2)

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

Decatrien-(4cis.6trans.8trans)-saeureethylester (18744-19-9) → Alpha-Sanshool (504-97-2)

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

hept-2-en-6-ynoic acid methyl ester (140677-99-2, 141943-16-0, 140677-83-4) → Alpha-Sanshool (504-97-2)

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

(E)-hept-2-en-6-ynoic acid (101861-38-5, 121318-58-9) → Alpha-Sanshool (504-97-2)

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

(E)-N-(2-methylpropyl)-2-hepten-6-ynamide (138691-20-0) → Alpha-Sanshool (504-97-2)

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

maleic anhydride (108-31-6) + Alpha-Sanshool (504-97-2) → (+/-)-3c-(6t-isobutylcarbamoyl-hexa-1,5-dien-c-yl)-6c-methyl-cyclohex-4-ene-1r,2c-dicarboxylic acid-anhydride (102461-89-2)

Conditions	Yield
With benzene

Alpha-Sanshool (504-97-2) → Beta-Sanshool (10076-00-3)

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

diethyl ether (60-29-7) + Alpha-Sanshool (504-97-2) + palladium → N-(2-methylpropyl)dodecanamide (68125-01-9)

Conditions	Yield
Hydrogenation;

Alpha-Sanshool (504-97-2) + acetic acid (64-19-7) + palladium → N-(2-methylpropyl)dodecanamide (68125-01-9)

Conditions	Yield
Hydrogenation;

Upstream product

• 18744-21-3 2E,6Z,8E,10E-dodecatetraenoic acid 
• 78-81-9 isobutylamine 
• 142-83-6 trans,trans-2,4-Hexadienal 
• 98095-55-7 (E)-6-(Triphenyl-λ⁵-phosphanylidene)-hex-2-enoic acid isobutyl-amide 
• 18744-20-2 Decatrien-(4cis.6trans.8trans)-saeure 
• 18744-19-9 Decatrien-(4cis.6trans.8trans)-saeureethylester 
• 140677-99-2 hept-2-en-6-ynoic acid methyl ester 
• 101861-38-5 (E)-hept-2-en-6-ynoic acid 
• 138691-20-0 (E)-N-(2-methylpropyl)-2-hepten-6-ynamide 

Downstream Products

• 68125-01-9 N-isobutyldodecanamide 

Relevant academic research and scientific papers

Method for producing sanshool

PROBLEM TO BE SOLVED: To provide a short-step, highly stereoselective method for producing sanshools, and an alkyne derivative that is an intermediate useful for the method.SOLUTION: The alkyne derivative is represented by general formula (I), wherein Arepresents a halogen atom; and R represents a hydrogen atom, hydroxy or methyl. The method for producing sanshools uses this alkyne derivative, and comprises a step of cross-coupling reacting the alkyne derivative with a boronic acid derivative.

SYNTHESIS OF NATURAL POLYENE ISOBUTYLAMIDES. STEREOCHEMISTRY OF THE WITTIG REACTIONS

Unsaturated isobutylamide synthons are employed to make seven natural amides.The (Z)-selectivity of the Wittig reaction towards the newly formed olefinic bond in the seven examples is estimated by 13Cmr.