83883-10-7

Usage

Uses

Used in Pharmaceutical Industry:
(2E,6Z,8E,10E)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide is used as a pharmaceutical compound for its potential reactivity and interactions in biological systems. The presence of the N-hydroxyalkyl group may allow for hydrogen bonding, which could be exploited in the development of new drugs or drug delivery systems.
Used in Materials Science:
In the field of materials science, (2E,6Z,8E,10E)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide may be utilized for its unique structural properties. （2E，6Z，8E，10E）-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide's high degree of unsaturation could contribute to the development of new materials with specific mechanical, electrical, or optical properties.
Used in Organic Synthesis:
(2E,6Z,8E,10E)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenamide is used as a synthetic intermediate in organic synthesis. Its conjugated double bonds and functional groups make it a versatile building block for the creation of more complex organic molecules, potentially leading to the discovery of new chemical entities with various applications.

Upstream product

• 97465-69-5 hydroxy-α-sanshool 
• 125521-30-4 (2E,4E)-hexa-2,4-dien-1-yl(triphenyl)phosphonium bromide 
• 70125-12-1 (Z)-6-Oxo-hex-2-enoic acid methyl ester 
• 63072-78-6 sorbyl bromide 
• 2854-16-2 1-Amino-2-methyl-propan-2-ol 
• 18744-21-3 2E,6Z,8E,10E-dodecatetraenoic acid 
• 71032-10-5 (E)-ethyl 6-bromohex-2-enoate 
• 21705-32-8 Ethyl 6-hydroxy-2Z-hexenoate 
• 140677-99-2 hept-2-en-6-ynoic acid methyl ester 
• 5390-04-5 pent-1-yn-5-ol 
• 101861-38-5 (E)-hept-2-en-6-ynoic acid 
• 1383002-43-4 (2E,8E,10E)-N-(2-hydroxy-2-methylpropyl)dodeca-2,8,10-trien-6-yneamide 
• 1383002-41-2 (E)-N-(2-hydroxy-2-methylpropyl)hept-2-en-6-ynamide 
• 1383002-42-3 (E)-7-bromo-N-(2-hydroxy-2-methylpropyl)hept-2-en-6-ynamide 

Downstream Products

• 83883-10-7 beta-Hydroxy-Sanshool 

Relevant academic research and scientific papers

DISTRIBUTION OF UNSATURATED ALIPHATIC ACID AMIDES IN JAPANESE ZANTHOXYLUM SPECIES

Seven species and two varieties of Zanthoxylum in Japan were investigated for unsaturated aliphatic acid amides.In addition to the known amides α-sanshooel, γ-sanshooel and hydroxy-γ-sanshooel, a new compound, hydroxy-α-sanshooel, was isolated and established by chemical and spectroscopic evidence.The compounds, corresponding to hydroxyl derivatives of the amides in the barks, commonly existed in the pericarps of all collected materials.Japanese Zanthoxylum species were divided chemotaxonomically into two taxa.These taxa differ from the two assigned on the basis of botanical classification.Key Word Index - Zanthoxylum planispinum; Z. piperitum; Z. piperitum f. inerme.Z. piperitum f. brevispinosum; Z. beecheyanum; Z. aliantholides; Z. inerme; Z. fauriei; Z. schinifolium; Rutaceae; α-sanshooel; hydroxy-α-sanshooel; γ-sanshooel; hydroxy-γ-sanshooel; unsaturated aliphatic acid amide; pungent principle; 13C NMR; chemotaxonomy; Fagara.

Synthesis of hydroxy-α-sanshool

Hydroxy-α-sanshool was synthesized in a 13% overall yield through eight steps, which included two Wittig reactions that were used to form the carbon skeleton with ethyl 2-oxoacetate and 2E,4E-hexadienal being reacted with the appropriate ylides. Impurities in the processes could easily be separated. Ethyl 6-hydroxy-2Z-hexenoate was converted to its E-isomer with catalysis by I2 and 2E,6Z,8E,10E-dodecatetraenoic acid was crystallized from a solution in 1% ethyl acetate in n-hexane.

Ruthenium-Catalyzed Direct Dehydrogenative Cross-Coupling of Allyl Alcohols and Acrylates: Application to Total Synthesis of Hydroxy β-Sanshool, ZP-Amide I, and Chondrillin

Ru-catalyzed oxidative coupling of allyl alcohols and activated olefins has been developed by C(allyl)-H activation of allyl alcohols providing efficient and direct access to synthetically useful α,β-unsaturated enone intermediates. Synthetic utility of this method was demonstrated by its application to synthesis of bioactive natural products such as Hydroxy-β-sanshool, ZP-amide I, Chondrillin, Plakorin, and (+)-cis-Solamin A.

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.

METHOD FOR PRODUCING SANSHOOL

Provided are a method for producing a sanshool, which method has a short process and exhibits high stereoselectivity, as well as an iron carbonyl complex compound that is an intermediate useful for the production method. A diene iron complex compound characterized by being represented by the following general formula (I): (in which A represents CO, P(RA)3, CN, NO, SO(RA)3, or N(RA)2; RA represents a straight chain or branched chain alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms; and one of R1 and R2 represents a hydrogen atom and the other one thereof represents a structure represented by the following formula (II)): (in which R represents a hydrogen atom, a hydroxyl group, or a methyl group).

Application of iron carbonyl complexation to the selective total synthesis of sanshools

We focused on the iron-complexes of sanshools (hydroxyl-α-sanshool, hydroxyl-β-sanshool, and γ-sanshool) as the key intermediates for the selective synthesis of these structurally unstable compounds. Consequently, we developed a concise and selective method for the total synthesis of sanshools in 5-6 steps (26-45% overall yield), including complexation of dienes with iron tricarbonyl group.

Total synthesis of hydroxy-α- and hydroxy-β-sanshool using Suzuki-Miyaura coupling

Here, we describe the first total synthesis of hydroxyl-α- and hydroxyl-β-sanshool, which involves Suzuki-Miyaura coupling (SMC). Hydroxy-α-sanshool (1) was synthesized by SMC of bromoalkyne 4 with boronate 3 followed by (Z)-selective reduction of the triple bond in the coupling product. Hydroxy-β-sanshool (2) was synthesized by regio- and (E)-selective conversion of 4 to iodoalkene 11 followed by SMC with 3.

Synthesis of hydroxy-α-sanshool

The amide hydroxy-α-sanshool is responsible for the mild numbing sensation experienced when Sichuan (or Szechuan) peppercorns (huajiao) are eaten. It has been synthesized in six steps from simple commercially available starting materials using Wittig reactions as the key transformations for construction of the carbon skeleton. The penultimate synthetic intermediate was 2E,6Z,8E,10E-dodecatetraenoic acid, and its crystalline nature allowed it, and thus hydroxy-α-sanshool, to be purified to a very high level of stereochemical homogeneity.