Trigonelline

ChemicalBook > CAS DataBase List > Trigonelline

Product Name: Trigonelline
CAS No.: 535-83-1
Chemical Name: Trigonelline
Synonyms: Gynesine;N-Methylnicotinate;Caffearine;Gynesis;Coffearin;Coffearine;Trigonellin;Trigoneline;Trigenolline;TRIGONELLINE
CBNumber: CB4415552
Molecular Formula: C7H7NO2
Formula Weight: 137.14
MOL File: 535-83-1.mol

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Trigonelline Property

Melting point:: 260°C (dec.)
Boiling point:: 251.96°C (rough estimate)
Density: 1.2528 (rough estimate)
refractive index: 1.5030 (estimate)
storage temp.: Refrigerator
solubility: Methanol (Slightly), Water (Slightly)
form: Solid
color: Off-White to Light Beige
LogP: -3.910 (est)

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Safety

Safety Statements: 24/25
HS Code: 29339900
Hazardous Substances Data: 535-83-1(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: T794000
Product name: Trigonelline
Packaging: 5g
Price: $415
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb104968
Product name: Trigonelline
Purity: >98%,Standard References Grade
Packaging: 20mg
Price: $569.5
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 62364
Product name: Trigonelline
Packaging: 100mg
Price: $720
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: PXT0005312
Product name: TRIGONELLINE
Purity: 95.00%
Packaging: 100MG
Price: $745.85
Updated: 2021/12/16

ApexBio Technology

Product number: N2788
Product name: Trigonelline
Packaging: 20mg
Price: $50
Updated: 2021/12/16

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Trigonelline Chemical Properties,Usage,Production

Description

Trigonelline is a bitter alkaloid in coffee which serves to produce important aroma compounds. In terms of concentration trigonelline is higher for arabica than robusta and ranges from about 0.6-1.3% and 0.3-0.9%, respectively.
Trigonelline, the N-methylpyridinium-3-carboxylate, is, after caffeine, the second most important alkaloid of coffee, with about 1% of the green bean. During leaf development, it is synthesized in the leaves and in the fruits' pericarp and accumulated in the seeds. The direct precursors are nicotinic acid and nicotine amide, deriving from the pyridine nucleotide cycle.
Trigonelline is a plant hormone that has diverse regulatory functions with respect to plant cell cycle regulation, nodulation, and oxidative stress, and in helping survival and growth of the plant. It is found in significant quantity in many plants like coffee beans and fenugreek seed. Because it was first isolated from the fenugreek seeds (Trigonella foenum-graecum), the name assigned to it has been “trigonelline.” The chemical formula for trigonelline is C7H7NO2. It is a methylation product of niacin (vitamin B3), and thus is also known as “methylated niacin.” At higher temperatures, trigonelline breaks down to niacin. In addition to trigonelline, fenugreek seeds contain other alkaloids such as gentianine and carpaine.

Chemical Properties

White solid

Uses

antihyperglycemic.
Trigonelline is an inhibitor which, like abscicic acid, accumulates in plant cells when the plant becomes dormant or is exposed to stress. This natural inhibitor is chemically related to glycine betaine. It has been found in dormant winter buds of Populus trichocarpa * deltoides trees in the field as well as in salt-stressed micropropagules thereof. Some trigonelline also occurred in non-stressed micropropagules, probably as the result of bioconversion of niacin taken up from the nutrient medium (Bray et al. 1988). Trigonelline preferentially promotes arrest in G2 of the cell cycle and appears to have a growth controlling function during seed germination (Evans and Tramontano 1981).

Uses

Trigonelline is an alkaloid present in coffee and fenugreek presenting phytoestrogenic activity.

Definition

ChEBI: An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.

Biosynthesis

Trigonelline is synthesized by the methylation of nicotinic acid. This reaction is catalyzed by Sadenosyl-L-methionine (SAM) dependent nicotinate N-methyltransferase (EC 2.1.1.7), which is found in crude extracts of the pea. This enzyme has now been purified from heterotrophic cultured cells and leaves of Glycine max. The Km values for nicotinate and SAM were 78 μM and 55 μM, respectively in the enzyme derived from cultured cells, and 12.5 μM and 31 μM in leaves. The optimum pH of the cultured cell enzyme is alkaline (8.0), but that of the leaf enzyme is acidic (6.5). The gene encoding trigonelline synthase has not yet been cloned from any organism.

Purification Methods

Crystallise trigonelline (as monohydrate) from aqueous EtOH, then dry it at 100o. It also crystallises from H2O as the monohydrate with m 230-233o(dec). It has been crystallised from EtOH with m 214-215o(dec). The picrate crystallises from EtOH with m 204-206o. [Green & Tong J Am Chem Soc 78 4896 1956, Kosower & Patton J Org Chem 26 1319 1961, Beilstein 22 III/IV 462, 22/2 V 143.]

References

Jahns., Ber., 18,2518 (1885)
Thoms., ibid, 31,271,404 (1891)
Schultz, Frankfurt., ibid, 27,709 (1894)
Gorter., Annalen, 372,237 (1910)
Schultz, Trier., Zeit. physiol. Chem., 76,258 (1912)
Holtz, Kutscher, Theilmann., Zeit. Bioi., 8, 57 (1924)
Rimington., Onderstepoort J., 5, 81 (1935)
Pharmacology :
Ackermann., Zeit. Bioi., 59, 17 (1912)
Volmer, Furst., Bull. Acad. Med., 122,241 (1939)

Trigonelline Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Trigonelline manufacturers

Baoji Guokang Bio-Technology Co., Ltd.

Product: Trigonelline 535-83-1
Price: US $269.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100kg
Release date: 2021-06-08

Zhuozhou Wenxi import and Export Co., Ltd

Product: Trigonelline 535-83-1
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: Trigonelline 535-83-1
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-08

535-83-1, TrigonellineRelated Search:

Rosmarinic acid ELEUTHEROSIDE E1 Astragaloside A Banaba Leaf Extract Common Fenugreek Seed P.E. Vitexin N-Benzylniacin 1-BENZYL-3-SODIUMCARBOXY-PYRIDINIUM CHLORIDE Trigonelline chloride,TRIGONELLINE HCL,TRIGONELLINE HYDROCHLORIDE TRIGONELLINE HCL Trigonelline Trigonelline amide TRIGONELLINE(RG) NIACIN RIBOSIDE, [CARBOXYL-14C]- Trigonelline sulfate TRIGONELLINE MONOHYDRATE 1-METHYL-2-SULFANYLPYRIDINIUM-3-CARBOXYLATE SPECS AJ-333/25022083

betainnicotinate

Caffearine

Coffearin

Coffearine

Gynesine

n’-methylnicotinicacid

Nicotinic acid N-methylbetaine

nicotinicacidn-methylbetaine

N-Methylnicotinate

N'-Methylnicotinic acid

N-Methylnicotinic acid

n-methylnicotinicacid

Trigonelline, froM Trigonella foenuM-graecuM

Trigonelline, 98%, from Trigonella foenum-graecum L.

Trigonelline, 98%, from Trigonella foenum-graecum

Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt

pyridinium,3-carboxy-1-methyl-,hydroxide,innersalt

Trigenolline

Trigonellin

TRIGONELLINE

RARECHEM AQ NN 0202

SPECS AP-163/40806827

1-methylpyridinio-3-carboxylate

1-methylpyridine-5-carboxylate

1-Methyl-3-pyridiniumcarboxylate

3-Carboxy-1-methylpyridinium hydroxide inner salt

3-carboxy-1-methylpyridiniumhydroxideinnersalt

Betain nicotinate

Betaine nicotinate

betainenicotinate

1-Methylpyridinium-3-carboxylate

Gynesis

N-Methylnicotinic betaine

Trigoneline

535-83-1

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

Inhibitors