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Capsiate is a capsinoid compound, a non-pungent capsaicin analog that can promote metabolic health and exercise tolerance.

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  • 205687-01-0 Structure
  • Basic information

    1. Product Name: CAPSIATE
    2. Synonyms: CAPSIATE;(E)-8-Methyl-6-nonenoic acid (4-hydroxy-3-methoxyphenyl)methyl ester;CH-19 Capsiate
    3. CAS NO:205687-01-0
    4. Molecular Formula: C18H26O4
    5. Molecular Weight: 306.4
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 205687-01-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 421.3±40.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.053
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: 9.51±0.20(Predicted)
    10. CAS DataBase Reference: CAPSIATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: CAPSIATE(205687-01-0)
    12. EPA Substance Registry System: CAPSIATE(205687-01-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 205687-01-0(Hazardous Substances Data)

205687-01-0 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.

Check Digit Verification of cas no

The CAS Registry Mumber 205687-01-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,5,6,8 and 7 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 205687-01:
(8*2)+(7*0)+(6*5)+(5*6)+(4*8)+(3*7)+(2*0)+(1*1)=130
130 % 10 = 0
So 205687-01-0 is a valid CAS Registry Number.

205687-01-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (90526)  Capsiate  analytical standard

  • 205687-01-0

  • 90526-25MG

  • 3,601.26CNY

  • Detail

205687-01-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (4-hydroxy-3-methoxyphenyl)methyl (E)-8-methylnon-6-enoate

1.2 Other means of identification

Product number -
Other names Capsiate Natura

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:205687-01-0 SDS

205687-01-0Synthetic route

trans-8-methyl-6-nonenoic acid
59320-77-3

trans-8-methyl-6-nonenoic acid

4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

capsiate
205687-01-0

capsiate

Conditions
ConditionsYield
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

4-t-butyldimethylsilyloxy-3-methoxybenzyl (E)-8-methylnon-6-enoate

capsiate
205687-01-0

capsiate

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol at 20℃; for 18h; Inert atmosphere;79.42%
8-methylnonanoic acid methyl ester
5129-54-4

8-methylnonanoic acid methyl ester

methyl isononanoate
5129-53-3

methyl isononanoate

4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

(E)-methyl 8-methyl-6-nonenoate
112375-54-9

(E)-methyl 8-methyl-6-nonenoate

A

Dihydrocapsiate

Dihydrocapsiate

B

capsiate
205687-01-0

capsiate

C

Nordihydrocapsiate

Nordihydrocapsiate

Conditions
ConditionsYield
novozyme 435 at 25℃; for 45h;
trans-8-methyl-6-nonenoic acid
59320-77-3

trans-8-methyl-6-nonenoic acid

capsiate
205687-01-0

capsiate

Conditions
ConditionsYield
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

O-tert-butyldimethylsilylvanillin

capsiate
205687-01-0

capsiate

Conditions
ConditionsYield
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

vanillin

capsiate
205687-01-0

capsiate

Conditions
ConditionsYield
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

(6Z)-8-methyl-6-nonaneneoic acid

capsiate
205687-01-0

capsiate

Conditions
ConditionsYield
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

(E)-8-Methylnon-6-enoic acid chloride

4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl alcohol
113931-96-7

4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl alcohol

capsiate
205687-01-0

capsiate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 18 h / Inert atmosphere
2: hydrogenchloride; water / ethanol / 18 h / 20 °C / Inert atmosphere
View Scheme
capsiate
205687-01-0

capsiate

A

O-[4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-methoxybenzyl]-8-methyl-6-nonenoic acid ester

O-[4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-methoxybenzyl]-8-methyl-6-nonenoic acid ester

B

C32H44O13

C32H44O13

Conditions
ConditionsYield
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

205687-01-0Downstream Products

205687-01-0Relevant 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

Barbero, Gerardo F.,Molinillo, Jose M. G.,Varela, Rosa M.,Palma, Miguel,MacIas, Francisco A.,Barroso, Carmelo G.

, p. 3342 - 3349 (2011/07/30)

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

-

Page/Page column 8, (2010/03/02)

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

-

Page/Page column 13, (2008/12/04)

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

-

Page/Page column 8, (2008/06/13)

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

-

Page/Page column 40-41, (2008/06/13)

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

Appendino, Giovanni,Minassi, Alberto,Daddario, Nives,Bianchi, Federica,Tron, Gian Cesare

, p. 3839 - 3841 (2007/10/03)

(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.

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