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

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

Used in Health and Fitness Industry:
Capsiate is used as a metabolic enhancer for promoting weight management and improving exercise tolerance. It helps to increase the body's metabolic rate, which can aid in burning calories and reducing body fat. Additionally, it can improve physical performance and endurance during exercise, making it a valuable supplement for athletes and fitness enthusiasts.

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

• 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 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 
• 59320-77-3 trans-8-methyl-6-nonenoic acid 
• 1073340-78-9 4-t-butyldimethylsilyloxy-3-methoxybenzyl (E)-8-methylnon-6-enoate 
• 5129-54-4 8-methylnonanoic acid methyl ester 
• 5129-53-3 methyl isononanoate 
• 498-00-0 4-hydroxymethyl-2-methoxyphenol 
• 112375-54-9 methyl (E)-8-methyl-6-nonenoate 

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.

METHOD FOR THE CHEMICAL SYNTHESIS OF CAPSINOIDS

Method for the chemical synthesis of capsinoids, natural compounds with proven biological activity, from vanillin, comprising the protection of the alcohol group thereof, reduction of the aldehyde to alcohol, esterification of same and deprotection of the first protected alcohol group. In this way, the desired compounds are generated with high purity and said compounds can be easily separated with no mixing owing to the competitive esterification on the aromatic ring.

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):

PRODUCTION METHOD OF CAPSINOID BY DEHYDRATING CONDENSATION, STABILIZING METHOD OF CAPSINOID, AND CAPSINOID COMPOSITION

In the production methods of capsinoid by esterification using an enzyme, a method of conveniently obtaining capsinoid in a high yield in a short time without using a dehydrating agent is provided. In addition, a method of stable preservation of produced capsinoid by purifying the obtained capsinoid under stable conditions is provided. A fatty acid represented by the formula (1) and a hydroxymethylphenol represented by the formula (2) are condensed without solvent or in a low-polar solvent, using an enzyme as a catalyst to give an ester compound represented by the formula (3). In addition, a fatty acid represented by the formula (4) is added to the ester compound represented by the formula (3) for stabilization. wherein each symbol is as defined in the specification.

Chemoselective Esterification of Phenolic Acids and Alcohols

(Matrix Presented) The Mitsunobu reaction can distinguish between alcohol and phenol hydroxyls in esterification reactions, providing an expeditious and broadly applicable entry into various phenolics and polyphenolics of biomedical and nutritional relevance.