205687-01-0

Basic information

• Product Name: CAPSIATE
• Synonyms: CAPSIATE;(E)-8-Methyl-6-nonenoic acid (4-hydroxy-3-methoxyphenyl)methyl ester;CH-19 Capsiate
• CAS NO: 205687-01-0
• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.4
• Mol File: 205687-01-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 421.3±40.0 °C(Predicted)
• Appearance: /
• Density: 1.053
• PKA: 9.51±0.20(Predicted)
• CAS DataBase Reference: CAPSIATE(CAS DataBase Reference)
• NIST Chemistry Reference: CAPSIATE(205687-01-0)
• EPA Substance Registry System: CAPSIATE(205687-01-0)

Safety Data

• Hazardous Substances Data: 205687-01-0(Hazardous Substances Data)

Usage

Uses

Capsiate is a capsinoid compound which are non-pungent capsaicin analogs that can promote metabolic health and exercise tolerance.

Synthetic route

trans-8-methyl-6-nonenoic acid (59320-77-3) + 4-hydroxymethyl-2-methoxyphenol (498-00-0) → capsiate (205687-01-0)

Conditions	Yield
Novozym 435 at 50℃; for 16h; Polyacrylate;	86.6%
With di-isopropyl azodicarboxylate; thiamine diphosphate In tetrahydrofuran at 20℃; Mitsunobu esterification;	51%

4-t-butyldimethylsilyloxy-3-methoxybenzyl (E)-8-methylnon-6-enoate (1073340-78-9) → capsiate (205687-01-0)

Conditions	Yield
With hydrogenchloride; water In ethanol at 20℃; for 18h; Inert atmosphere;	79.42%

8-methylnonanoic acid methyl ester (5129-54-4) + methyl isononanoate (5129-53-3) + 4-hydroxymethyl-2-methoxyphenol (498-00-0) + (E)-methyl 8-methyl-6-nonenoate (112375-54-9) → Dihydrocapsiate + capsiate (205687-01-0) + Nordihydrocapsiate

Conditions	Yield
novozyme 435 at 25℃; for 45h;

trans-8-methyl-6-nonenoic acid (59320-77-3) → capsiate (205687-01-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / 1 h / 60 °C 2: pyridine / 18 h / Inert atmosphere 3: hydrogenchloride; water / ethanol / 18 h / 20 °C / Inert atmosphere View Scheme

O-tert-butyldimethylsilylvanillin (69404-94-0) → capsiate (205687-01-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 48 h / 20 °C / Cooling with ice; Inert atmosphere 2: pyridine / 18 h / Inert atmosphere 3: hydrogenchloride; water / ethanol / 18 h / 20 °C / Inert atmosphere View Scheme

vanillin (121-33-5) → capsiate (205687-01-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 24 h / 20 °C / Inert atmosphere 2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 48 h / 20 °C / Cooling with ice; Inert atmosphere 3: pyridine / 18 h / Inert atmosphere 4: hydrogenchloride; water / ethanol / 18 h / 20 °C / Inert atmosphere View Scheme

(6Z)-8-methyl-6-nonaneneoic acid (31467-60-4) → capsiate (205687-01-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: nitric acid; sodium nitrite / water / 1.5 h / 70 °C / Inert atmosphere 2: thionyl chloride / 1 h / 60 °C 3: pyridine / 18 h / Inert atmosphere 4: hydrogenchloride; water / ethanol / 18 h / 20 °C / Inert atmosphere View Scheme

(E)-8-Methylnon-6-enoic acid chloride (95636-02-5) + 4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl alcohol (113931-96-7) → capsiate (205687-01-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 18 h / Inert atmosphere 2: hydrogenchloride; water / ethanol / 18 h / 20 °C / Inert atmosphere View Scheme

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3) + capsiate (205687-01-0) → O-[4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-methoxybenzyl]-8-methyl-6-nonenoic acid ester + C32H44O13

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In toluene at 20℃; for 17h; Cooling with ice; Overall yield = 67 %; Overall yield = 4.58 g;	A n/a B n/a

Upstream product

• 59320-77-3 trans-8-methyl-6-nonenoic acid 
• 498-00-0 4-hydroxymethyl-2-methoxyphenol 
• 5129-54-4 8-methylnonanoic acid methyl ester 
• 5129-53-3 methyl isononanoate 
• 112375-54-9 methyl (E)-8-methyl-6-nonenoate 
• 1073340-78-9 4-t-butyldimethylsilyloxy-3-methoxybenzyl (E)-8-methylnon-6-enoate 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 
• 121-33-5 vanillin 
• 31467-60-4 (6Z)-8-methyl-6-nonaneneoic acid 
• 95636-02-5 (E)-8-Methylnon-6-enoic acid chloride 
• 113931-96-7 4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl alcohol 

Relevant articles and documents

Application of hansch's model to capsaicinoids and capsinoids: A study using the quantitative structure-activity relationship. A novel method for the synthesis of capsinoids

We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestlvum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.

CAPSINOID CONTAINING COMPOSITION

Problem to be Solved To provide a technique for allowing pulverization and water-solubilization of capsinoids while maintaining their stability. Solution Providing a composition comprising a capsinoid compound and cyclodextrin.

Topically applied circulation enhancing agent and skin and hair cosmetic and bath agent containing the same

A topically applied circulation enhancing agent suited for application over the entire body which has good transdermal absorptivity and causes little irritation is provided. A topically applied circulation enhancing agent is provided which contains a fatty acid ester denoted by general formula (1):