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149-91-7

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149-91-7 Usage

Description

Different sources of media describe the Description of 149-91-7 differently. You can refer to the following data:
1. Gallic acid is a tri hydroxy benzoic acid, a type of phenolic acid, a type of organic acid, also known as 3,4,5- tri hydroxy benzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3COOH. Gallic acid is found both free and as part of hydrolyzable tannins. Salts and esters of gallic acid are termed 'gallates'. Despite its name, it does not contain gallium. Gallic acid is commonly used in the pharmaceutical industry. It is used as a standard for determining the phenol content of various analytes by the Folin - Ciocalteau assay; results are reported in gallic acid equivalents. Gallic acid can also be used as a starting material in the synthesis of the psychedelic alkaloid mescaline. Gallic acid seems to have anti-fungal and anti - viral properties. Gallic acid acts as an antioxidant and helps to protect human cells against oxidative damage. Gallic acid was found to show cytotoxicity against cancer cells, without harming healthy cells. Gallic acid is used as a remote astringent in cases of internal haemorrhage. Gallic acid is also used to treat albuminuria and diabetes. Some ointments to treat psoriasis and external haemorrhoids contain gallic acid.
2. Gallic acid is a phenol that has been found in C. sinensis and has diverse biological activities. It scavenges DPPH and hydroxyl radicals in cell-free assays (IC50s = 9.4 and 191 μM, respectively). Gallic acid (1-100 μM) reverses abscisic acid-induced inhibition of hypocotyl growth in A. caudatus seedlings. In vivo, gallic acid (21.8 g/kg) inhibits morpholine- and sodium nitrite-induced adenocarcinoma formation in mice. It also inhibits passive cutaneous anaphylaxis in mice when administered at a dose of 50 mg/kg.

Chemical Properties

Colorless crystalline needles or prisms obtained from nutgall tannins,gallic acid is soluble in water and alcohol and melts at 235 to 240 °C. Also known as trihydroxybenzoic acid, it is used in photography, tanning, ink manufacture and pharmaceuticals.

Occurrence

Gallic acid is found in a number of land plants. It is also found in the aquatic plant Myriophyllum spicatum and shows an allelopathic effect on the growth of the blue-green alga Microcystis aeruginosa. In food Areca nut Bearberry (Arctostaphylos sp) Bergenia sp Blackberry Hot chocolate Juglans regia (Common walnut) Mango in peels and leaves Phyllanthus emblica (Indian gooseberry) in fruits Raspberry Syzygium aromaticum (clove) Vinegar wine Witch hazel (Hamamelis virginiana) White tea.

Uses

Different sources of media describe the Uses of 149-91-7 differently. You can refer to the following data:
1. Gallic acid is an important component of iron gall ink, the standard European writing and drawing ink from the 12 th to 19th century with a history extending to the Roman empire and the Dead Sea Scrolls. Pliny the Elder (23-79 AD) describes his experiments with it and writes that it was used to produce dyes. Galls (also known as oak apples) from oak trees were crushed and mixed with water, producing tannic acid (a macromolecular complex containing gallic acid). It could then be mixed with green vitriol (ferrous sulfate) — obtained by allowing sulfate - saturated water from a spring or mine drainage to evaporate — and gum arabic from acacia trees; this combination of ingredients produced the ink. Gallic acid was one of the substances used by Angelo Mai (1782–1854), among other early investigators of palimpsests, to clear the top layer of text off and reveal hidden manuscripts underneath. Mai was the first to employ it, but did so "with a heavy hand", often rendering manuscripts too damaged for subsequent study by other researchers. Early photographers, including Joseph Bancroft Reade (1801– 1870) and William Fox Talbot (1800 – 1877), used gallic acid for developing latent images in calotypes. It has also been used as a coating agent in zincography.
2. It can be used to produce polyesters based on phloretic acid and gallic acid.
3. gallic acid is a potential bleaching agent and anti-oxidant, it is also astringent and potentially anti-microbial and anti-fungal. Scientists are finding that gallic acid may serve as a skin-lightening agent by inhibiting the action of the tyrosinase and peroxidase enzymes. Some studies indicate that it is more effective than hydroquinone when combined with the proper ingredients. It is also incorporated into anti-aging formulations for its ability to prevent mucopolysaccaride deterioration. It is a constituent of witch hazel and oak bark, among many other plants; however, it is generally obtained from nutgalls for commercial purposes.
4. antineoplastic, astringent, antibacterial
5. Gallic acid is a trihydroxybenzoic acid found in many plants as either the free acid or in the esterified form of gallotannins and ellagitannins. It demonstrates antioxidant activity by scavenging 2,2-diphenyl-1-picrylhydrazyl and hydroxyl free radicals with IC50 values of 9.4 and 191 μM, respectively, and inhibiting microsomal lipid peroxidation with an IC50 value of 1.51 μM. Gallic acid is often used as a standard for determining the phenol content of various analytes by the Folin-Ciocalteau assay where results are reported in gallic acid equivalents.[Cayman Chemical]
6. A cyclooxygease inhibitor substance found in plants.

Definition

ChEBI: A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5.

Biotechnological Production

The production of gallic acid is challenging. Conventionally, it has been produced by acid hydrolysis of tannic acid. However, this process is expensive due to low yields and high impurities. To overcome this problem, microbial production of gallic acid has been suggested. For example, in a solid-state fermentation of Teri pod cover powder containing tannin using Rhizopus oryzae, a yield of 90.9 % based on the tannin content of 58 % of the substrate was observed. In a submerged culture of Aspergillus aceleatus DBF9 growing on a medium with 3 % tannin, a maximal product concentration of 6.8 g.L-1 was reported. With tannic acid, even higher product concentrations of up to 25 g.L-1, a yield of 0.83 g of gallic acid per gram of tannic acid, and a productivity of 0,56 g.L-1.h-1 were shown using Apergillus fischeri MTCC 150 in submerged cultivation. An alternative is the enzymatic hydrolysis of tannic acids using tannase produced by microorganisms (e.g. Aspergillus fischeri or R. oryzae). For example, propyl gallate could be produced using a tannase from Emericela nidulans immobilized on ionic and covalent supports.

General Description

Odorless white solid. Sinks in water.

Air & Water Reactions

Sparingly water soluble

Reactivity Profile

Phenols, such as Gallic acid, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid.

Health Hazard

Inhalation of dust may irritate nose and throat. Contact with eyes or skin causes irritation.

Fire Hazard

Flash point data for Gallic acid are not available. Gallic acid is probably combustible.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Gallic acid is a water soluble phenolic acid present in grapes and in the leaves of many plants. Gallic acid esters, such as tannins, catechin gallates and aliphatic gallates are potent antioxidants in vitro. However, gallic acid itself also appears to have antioxidant, anticarcinogenic and antiangiogenic activity in vitro.

Side effects

It is a weak carbonic anhydrase inhibitor.

Metabolism

Biosynthesis Chemical structure of 3,5- didehydro shikimate Gallic acid is formed from 3-dehydro shikimate by the action of the enzyme shikimate dehydro genase to produce 3,5-didehydro shikimate. This latter compound tautomerizes to form the redox equivalent gallic acid, where the equilibrium lies essentially entirely toward gallic acid because of the coincidently occurring aromatization. Degradation Gallate dioxygenase is an enzyme found in Pseudomonas putida that catalyzes the reaction : gallate + O2 → (1E)-4-oxobut-1-ene-1,2,4-tri carboxylate. Gallate decarboxylase is another enzyme in the degradation of gallic acid. Conjugation Gallate 1-beta-glucosyltransferase is an enzyme that uses UDPglucose and gallate, whereas its two products are UDP and 1-galloylbeta- D-glucose.

Purification Methods

Crystallise gallic from water. The tri-O-acetyl derivative has m 172o (from MeOH), and the anilide has m 207o(from EtOH). [Beilstein 10 H 470, 10 IV 1993.]

Esters

Also known as galloylated esters: Methyl gallate Ethyl gallate, a food additive with E number E313 Propyl gallate, or propyl 3,4,5-trihydroxybenzoate, an ester formed by the condensation of gallic acid and propanol Octyl gallate, the ester of octanol and gallic acid Dodecyl gallate, or lauryl gallate, the ester of dodecanol and gallic acid Epicatechin gallate, a flavan-3-ol, a type of flavonoid, present in green tea Epigallocatechin gallate (EGCG), also known as epigallocatechin 3-gallate, the ester of epigallocatechin and gallic acid, and a type of catechin Gallocatechin gallate (GCG), the ester of gallocatechin and gallic acid and a type of flavan-3ol Theaflavin-3-gallate, a theaflavin derivative.

Check Digit Verification of cas no

The CAS Registry Mumber 149-91-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 9 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 149-91:
(5*1)+(4*4)+(3*9)+(2*9)+(1*1)=67
67 % 10 = 7
So 149-91-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,8-10H,(H,11,12)

149-91-7 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Alfa Aesar

  • (B24887)  3,4,5-Trihydroxybenzoic acid, anhydrous, 99%   

  • 149-91-7

  • 250g

  • 705.0CNY

  • Detail
  • Alfa Aesar

  • (B24887)  3,4,5-Trihydroxybenzoic acid, anhydrous, 99%   

  • 149-91-7

  • 1000g

  • 2244.0CNY

  • Detail
  • Alfa Aesar

  • (B24887)  3,4,5-Trihydroxybenzoic acid, anhydrous, 99%   

  • 149-91-7

  • 5000g

  • 5116.0CNY

  • Detail
  • Sigma-Aldrich

  • (91215)  Gallicacid  certified reference material, TraceCERT®

  • 149-91-7

  • 91215-100MG

  • 1,075.23CNY

  • Detail

149-91-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name gallic acid

1.2 Other means of identification

Product number -
Other names 3,4,5-trihydroxybenzenoic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:149-91-7 SDS

149-91-7Synthetic route

tannic acid

tannic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With water at 80℃; for 6h; Reagent/catalyst;96.99%
tannic acid

tannic acid

A

D-Glucose
2280-44-6

D-Glucose

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With water at 60℃; for 6h; Reagent/catalyst;A n/a
B 91.5%
Eudesmic acid
118-41-2

Eudesmic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With pyridinium hydrobromide perbromide In xylene for 1.5h; Heating;75%
With hydrogen iodide
(-)-3-dehydroshikimic acid
2922-42-1

(-)-3-dehydroshikimic acid

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With copper diacetate In water; acetic acid at 40℃; for 36h; Oxidation; aromatization;A 0.7%
B 62%
With copper diacetate; oxygen; zinc(II) oxide In acetic acid at 50℃; under 760.051 Torr; for 14h; Kinetics; Product distribution; Further Variations:; Reagents; Oxidation; aromatization;
propan-1-ol
71-23-8

propan-1-ol

methyl galloate
99-24-1

methyl galloate

A

Propyl gallate
121-79-9

Propyl gallate

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With tannase from Lactobacillus plantarum immobilised on glyoxyl-agarose at 25℃; pH=5; aq. acetate buffer; Enzymatic reaction;A 55%
B n/a
gallaldehyde
13677-79-7

gallaldehyde

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With potassium bromate; hydrogenchloride; potassium bromide In water for 12h; Time;53%
glyceroltripalmitate
555-44-2

glyceroltripalmitate

Propyl gallate
121-79-9

Propyl gallate

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

3-((3',4',5'-trihydroxybenzoyl)oxy)propane-1,2-diyl dipalmitate

3-((3',4',5'-trihydroxybenzoyl)oxy)propane-1,2-diyl dipalmitate

Conditions
ConditionsYield
With recombinant lipase B from Candida antarctica, expressed in Aspergillus niger, and immobilized on a macroporous hydrophobic resin In neat (no solvent) at 70℃; for 120h; Catalytic behavior; Time; Enzymatic reaction;A n/a
B 33.02%
oolongtheanin 3'-O-gallate

oolongtheanin 3'-O-gallate

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

C36H24O16

C36H24O16

C

C36H26O16

C36H26O16

D

C43H32O21

C43H32O21

Conditions
ConditionsYield
With water at 60℃; for 4h;A 24.7%
B 3.3%
C 5.6%
D 5.6%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With sodium dihydrogenphosphate at 25℃; for 0.25h; pH=7; Glovebox;15%
Multi-step reaction with 2 steps
1: bromine
2: bei der Kalischmelze
View Scheme
(-)-3-dehydroshikimic acid
2922-42-1

(-)-3-dehydroshikimic acid

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

tricarallylic acid
99-14-9

tricarallylic acid

C

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

D

dihydrogallic acid
184105-29-1

dihydrogallic acid

E

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
With air; Na1.5H1.5PO4 at 40℃; for 50h; Rate constant; Mechanism; other oxidant, var. time;A 12 % Spectr.
B 14 % Spectr.
C 13%
D n/a
E 3 % Spectr.
tetrachloromethane
56-23-5

tetrachloromethane

3,4,5-tris[(methoxycarbonyl)oxy]benzoic acid
222320-76-5

3,4,5-tris[(methoxycarbonyl)oxy]benzoic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
at 20℃;
5-methylpyrogallol
609-25-6

5-methylpyrogallol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide beim Schmelzen;
3,5-diiodo-4-hydroxybenzoic acid
618-76-8

3,5-diiodo-4-hydroxybenzoic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide beim Schmelzen;
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide beim Schmelzen;
3-bromo-4,5-dihydroxybenzoic acid
61203-46-1

3-bromo-4,5-dihydroxybenzoic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide beim Schmelzen;
bei der Kalischmelze;
3,5-dibromo-4-hydroxybenzoic acid
3337-62-0

3,5-dibromo-4-hydroxybenzoic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With barium dihydroxide; water at 175℃; im Kupferkessel;
With potassium hydroxide; copper(I) sulfate; water; copper(II) sulfate at 150℃;
myricetin
529-44-2

myricetin

A

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide at 130℃; for 1.5h;
durch Kalischmelze;
4-galloyloxy-benzoic acid
685876-41-9

4-galloyloxy-benzoic acid

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

chebulic acid
84026-83-5

chebulic acid

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

sanguiin H-3

sanguiin H-3

A

alpha-D-glucopyranose
492-62-6

alpha-D-glucopyranose

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

C

tetramethylellagic acid
2080-25-3

tetramethylellagic acid

D

sanguisorbic acid dilactone heptamethyl ether
82203-12-1

sanguisorbic acid dilactone heptamethyl ether

Conditions
ConditionsYield
With sulfuric acid 1.) reflux, 7.5 h, 2.) ether, overnight; Yield given. Multistep reaction. Yields of byproduct given;
2,3-di-O-galloyl-D-4C1-glucopyranose
96691-90-6

2,3-di-O-galloyl-D-4C1-glucopyranose

A

D-glucose
50-99-7

D-glucose

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 3h;
With hydrogenchloride at 100℃; for 3h;
quercetin-3-O-(2”-galloyl)-β-D-galactopyranoside
53209-27-1, 69624-79-9

quercetin-3-O-(2”-galloyl)-β-D-galactopyranoside

A

Hyperoside
482-36-0

Hyperoside

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With tannase In water at 37℃; for 2h;
3,4,5-Trihydroxy-benzoic acid (2R,3S,4S,5R,6S)-6-(2,6-dihydroxy-4-hydroxymethyl-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester
67771-98-6

3,4,5-Trihydroxy-benzoic acid (2R,3S,4S,5R,6S)-6-(2,6-dihydroxy-4-hydroxymethyl-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

3,4,5-trihydroxybenzyl alcohol 4-O-β-D-glucopyranoside
64121-97-7

3,4,5-trihydroxybenzyl alcohol 4-O-β-D-glucopyranoside

Conditions
ConditionsYield
With tannase for 0.5h; Ambient temperature; incubation;A 29 mg
B 61 mg
2',5-di-O-galloyl-D-hamamelofuranose
99786-30-8, 102489-93-0, 102489-94-1

2',5-di-O-galloyl-D-hamamelofuranose

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

2-hydroxymethyl-D-ribose
469-33-0, 86420-47-5, 86420-48-6

2-hydroxymethyl-D-ribose

Conditions
ConditionsYield
With tannase In water at 37℃; for 1.5h; hydrolysis of other O-galloyl-D-hamameloses;
With tannase In water at 37℃; for 1.5h;A n/a
B 70 mg
methyl 3,5-dihydroxy-4-methoxybenzoate
24093-81-0

methyl 3,5-dihydroxy-4-methoxybenzoate

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With hydrogen iodide; acetic anhydride at 145℃; for 0.5h;
(-)-shikimic acid 3-O-gallate
95719-51-0

(-)-shikimic acid 3-O-gallate

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

shikimic acid
138-59-0

shikimic acid

Conditions
ConditionsYield
tannase In water at 37℃; for 3h; Product distribution;A 40 mg
B 43 mg
11-O-(3',4',5'-trihydroxygalloyl)bergenin
82958-44-9

11-O-(3',4',5'-trihydroxygalloyl)bergenin

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

bergenin
477-90-7

bergenin

Conditions
ConditionsYield
With trifluoroacetic acid In water for 30h; Heating;
bergenin-4-O-gallate
82958-45-0

bergenin-4-O-gallate

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

bergenin
477-90-7

bergenin

Conditions
ConditionsYield
With trifluoroacetic acid In water for 30h; Heating;
euphorbin B-phenazine

euphorbin B-phenazine

A

1,3,4,6-tetra-O-galloyl-β-D-glucose
26922-99-6

1,3,4,6-tetra-O-galloyl-β-D-glucose

B

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

C

3,4,6-tri-O-galloyl-α/β-D-glucose

3,4,6-tri-O-galloyl-α/β-D-glucose

D

corilagin
23094-69-1

corilagin

Conditions
ConditionsYield
In water; acetone for 10h; Heating;A 4 mg
B 15 mg
C 4 mg
D 2 mg
carpinin B

carpinin B

A

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

B

carpinin D

carpinin D

Conditions
ConditionsYield
enzymatic hydrolysis with tannase;
methanol
67-56-1

methanol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

methyl galloate
99-24-1

methyl galloate

Conditions
ConditionsYield
With sulfuric acid for 6h; Heating;100%
With brominated modified sulfonic acid resin at 65℃; for 4h; Reagent/catalyst;99%
With sulfuric acid for 1.5h; Heating / reflux;97%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyldimethylsilyl 3,4,5-tri[(tert-butyldimethylsilyl)oxy]benzoate
185462-50-4

tert-butyldimethylsilyl 3,4,5-tri[(tert-butyldimethylsilyl)oxy]benzoate

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; silylation;98%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;91.9%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; Substitution;
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

3,4,5-trihydroxybenzoic-2,6-d2 acid

3,4,5-trihydroxybenzoic-2,6-d2 acid

Conditions
ConditionsYield
With water-d2; hydrogen chloride for 6h; Inert atmosphere; Reflux;99%
With Amberlyst 15; water-d2 at 90℃; for 24h; Substitution;
With nafion resin; water-d2 at 90℃; for 24h;
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

carboxymethyl-dodecyl-dimethyl-ammonium betaine
683-10-3

carboxymethyl-dodecyl-dimethyl-ammonium betaine

dodecyldimethylglycine gallate

dodecyldimethylglycine gallate

Conditions
ConditionsYield
In methanol at 25℃; for 1h;99%
propan-1-ol
71-23-8

propan-1-ol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Propyl gallate
121-79-9

Propyl gallate

Conditions
ConditionsYield
With brominated modified sulfonic acid resin at 100℃; for 5h;98%
With toluene-4-sulfonic acid at 107℃; under 9308.91 Torr; for 0.133333h; Temperature; Wavelength; Sealed tube; Microwave irradiation;94%
With cucurbit[6]uril-supported Keggin-type silicotungstic acid Q[6]-STA at 96.84℃; for 4h; Catalytic behavior; Time; Reagent/catalyst;94.7%
ethanol
64-17-5

ethanol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Ethyl gallate
831-61-8

Ethyl gallate

Conditions
ConditionsYield
With brominated modified sulfonic acid resin at 80℃; for 5h; Reagent/catalyst;98%
With toluene-4-sulfonic acid at 88℃; under 9308.91 Torr; for 0.133333h; Temperature; Wavelength; Time; Sealed tube; Microwave irradiation;96%
With sulfuric acid at 70℃;95%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
With cucumber juice at 30 - 35℃; for 48h; Inert atmosphere; Green chemistry;98%
With Citrobacter sp at 28℃; for 24h; enzymatic synthesis by bacterium in a mixed medium containing: 0.5percent maltose, 0.2percent (NH4)2HPO4, 0.1percent KH2PO4, 0.05percent KCl, 0.05percentMgSO4.7H2Oand 0.05percent yeast, pH=4.5;97.4%
With Cocos nucifera juice at 20℃; for 48h; Inert atmosphere;96%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

hexan-1-ol
111-27-3

hexan-1-ol

n-hexyl gallate
1087-26-9

n-hexyl gallate

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation;98%
With brominated hydrophobically modified sulfonic acid resin at 150℃; for 10h;92%
Stage #1: 3,4,5-trihydroxybenzoic acid; hexan-1-ol With diisopropyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: With dmap In tetrahydrofuran at 20℃; for 24h;
72%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

sodium gallate

sodium gallate

Conditions
ConditionsYield
With sodium carbonate In methanol at 20℃; Schlenk technique; Inert atmosphere;98%
With sodium ethoxide In ethanol Inert atmosphere; Reflux;
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

gallic acid persulfate

gallic acid persulfate

Conditions
ConditionsYield
With triethylamine sulfur trioxide; triethylamine In N,N-dimethyl-formamide at 86℃; for 1h; Microwave irradiation; Green chemistry;98%
1-octadecanol
112-92-5

1-octadecanol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

octadecyl 3,4,5-trihydroxybenzoate
10361-12-3

octadecyl 3,4,5-trihydroxybenzoate

Conditions
ConditionsYield
With cation exchange resin 731 In ethyl acetate at 80 - 85℃; Dean-Stark;97.2%
With toluene-4-sulfonic acid In 1,4-dioxane at 160℃;73%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 10h;61%
With naphthalene-2-sulfonate; methoxybenzene; nitrobenzene unter Entfernen des entstehenden Wassers;
With toluene-4-sulfonic acid In toluene at 125℃; for 4h; Temperature;
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

butan-1-ol
71-36-3

butan-1-ol

n-butyl gallate
1083-41-6

n-butyl gallate

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation;97%
With brominated modified sulfonic acid resin at 120℃; for 5h;96%
With toluene-4-sulfonic acid at 128℃; under 9308.91 Torr; for 0.15h; Temperature; Wavelength; Sealed tube; Microwave irradiation;93%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Hernandezine
6681-13-6

Hernandezine

C39H44N2O7*2C7H6O5

C39H44N2O7*2C7H6O5

Conditions
ConditionsYield
In ethanol at 20℃; for 0.5h;97%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

trimethyl orthoformate
149-73-5

trimethyl orthoformate

C9H8O6

C9H8O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 105℃; Inert atmosphere;97%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

C10H10O6

C10H10O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 103℃; for 8h; Temperature; Inert atmosphere;97%
octanol
111-87-5

octanol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation;96%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h;89%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h;89%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

C6H10N2O3*C7H6O5
1392812-94-0

C6H10N2O3*C7H6O5

Conditions
ConditionsYield
In methanol for 24h;96%
phosgene
75-44-5

phosgene

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

7-hydroxy-2-oxo-benzo[1,3]dioxole-5-carboxylic acid
408340-58-9

7-hydroxy-2-oxo-benzo[1,3]dioxole-5-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate; triethylamine In dichloromethane; water at 12℃; for 1h; Temperature;96%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Eudesmic acid
118-41-2

Eudesmic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 120℃; Concentration; Inert atmosphere;95.6%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

rufigallol
82-12-2

rufigallol

Conditions
ConditionsYield
With sulfuric acid at 80 - 120℃; for 5h; Autoclave;95%
With sulfuric acid at 100℃; Inert atmosphere;92.2%
With sulfuric acid for 0.025h; microwave irradiation;80%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

acetic anhydride
108-24-7

acetic anhydride

3,4,5-triacetoxybenzoic acid
6635-24-1

3,4,5-triacetoxybenzoic acid

Conditions
ConditionsYield
at 130℃; for 4h;95%
for 3h; Reflux;95%
With sulfuric acid at 21 - 75℃;93%
2,2'-biimidazole
492-98-8

2,2'-biimidazole

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

water
7732-18-5

water

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

[Ni(2,2'-biimidazole)2(OH2)2](3,4,5-tris-hydroxy-benzoate)2*4H2O

[Ni(2,2'-biimidazole)2(OH2)2](3,4,5-tris-hydroxy-benzoate)2*4H2O

Conditions
ConditionsYield
In water 2,2'-biimidazole added to a soln. of metal acetate in hot water, a soln.of 3,4,5-tris-hydroxy-benzoic acid in hot water added; concn., controlled evapn. at room temp. for 2-3 wk; elem. anal.;95%
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

isobutyl 3,4,5-trihydroxybenzoate
3856-05-1

isobutyl 3,4,5-trihydroxybenzoate

Conditions
ConditionsYield
With brominated hydrophobically modified sulfonic acid resin at 110℃; for 8h;94%
With toluene-4-sulfonic acid at 118℃; under 9308.91 Torr; for 0.15h; Temperature; Wavelength; Sealed tube; Microwave irradiation;92%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 10h;87%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

isopropyl alcohol
67-63-0

isopropyl alcohol

isopropyl 3,4,5-trihydroxybenzoate
1138-60-9

isopropyl 3,4,5-trihydroxybenzoate

Conditions
ConditionsYield
With brominated modified sulfonic acid resin at 85℃; for 7h;94%
With sulfuric acid at 120℃; for 2h;94%
With toluene-4-sulfonic acid at 92℃; under 9308.91 Torr; for 0.133333h; Temperature; Wavelength; Sealed tube; Microwave irradiation;93%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Penciclovir
39809-25-1

Penciclovir

C10H15N5O3*C7H6O5*H2O

C10H15N5O3*C7H6O5*H2O

Conditions
ConditionsYield
With water In ethanol at 20℃; for 24h;94%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

betaine
107-43-7

betaine

betaine gallate

betaine gallate

Conditions
ConditionsYield
In methanol at 60℃; for 12h; Inert atmosphere;93.32%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

acetic anhydride
108-24-7

acetic anhydride

triacetylgallic acid
855291-88-2

triacetylgallic acid

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 2.5h; Cooling with ice;92.6%
pentan-1-ol
71-41-0

pentan-1-ol

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

pentyl 3,4,5-trihydroxybenzoate
4568-93-8

pentyl 3,4,5-trihydroxybenzoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 148℃; under 9308.91 Torr; for 0.166667h; Temperature; Wavelength; Sealed tube; Microwave irradiation;92%
With brominated modified sulfonic acid resin at 135℃; for 8h;92%
With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation;83%
vanadocene

vanadocene

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

cyclopentadienylvanadium digallate

cyclopentadienylvanadium digallate

Conditions
ConditionsYield
In diethyl ether byproducts: C5H6, H2; (vac. or Ar); addn. of acid to V-complex in ether (20°C, 48 h); filtration, washing (ether), drying; elem. anal.;92%

149-91-7Related news

Unravelling the Gallic acid (cas 149-91-7) degradation pathway in bacteria: the gal cluster from Pseudomonas putida09/30/2019

Gallic acid (3,4,5‐trihydroxybenzoic acid, GA) is widely distributed in nature, being a major phenolic pollutant and a commonly used antioxidant and building‐block for drug development. We have characterized the first complete cluster (gal genes) responsible for growth in GA in a derivative of...detailed

Gallic acid (cas 149-91-7) mediated oxidation of pentachlorophenol by the Fenton reaction under mild oxidative conditions09/29/2019

BACKGROUND The present study demonstrates the decomposition of pentachlorophenol (PCP) by the Fenton reaction in the presence of gallic acid (GA). Unlike other studies, catalytic Fe2+ concentrations were used with respect to PCP in an effort to evaluate an environmentally benign Fenton system, s...detailed

Comparison of hypolipidemic activity of synthetic Gallic acid (cas 149-91-7)–linoleic acid ester with mixture of Gallic acid (cas 149-91-7) and linoleic acid, Gallic acid (cas 149-91-7), and linoleic acid on high-fat diet induced obesity in C57BL/6 Cr Slc mice09/28/2019

Hyperlipidemia is the major risk factors of heart disease such as atherosclerosis, stroke, and death. In the present study, we studied the effect of gallic acid (GA), linoleic acid (LA), mixture of GA and LA (MGL), and chemically synthesized gallic acid–linoleic acid ester (octadeca-9,12-dienyl...detailed

149-91-7Relevant articles and documents

6″-Galloylpicein and other phenolic compounds from Arctostaphylos uva-ursi

Olennikov,Chekhirova

, p. 1 - 7 (2013)

Phenolic compounds from leafy shoots of A. uva-ursi (Ericaceae) were studied. The new phenolic glycoside 6″-galloylpicein and 40 known compounds were isolated. Roots of A. uva-ursi afforded 16 compounds. A C-glycoside of bergenin was found for the first time in the family Ericaceae. The dominant components of A. uva-ursi leaves according to HPLC were arbutin, (+)-catechin, and corilagin; of stems, picein and (+)-gallocatechingallate; of roots, (-)-epicatechin, (-)-epicatechingallate, and (+)-catechin.

Chemical transformation of oolongtheanin 3′-O-gallate in aqueous solution under heating conditions

Ochiai, Yuto,Ogawa, Kazuki,Sawada, Yoshiharu,Yanase, Emiko

, (2021)

To understand the stability of oolongtheanin 3′-O-gallate (1), present in oolong tea leaves, its chemical transformation in aqueous solution was investigated under heating conditions. Four compounds were obtained from 1, which were isolated and their chem

Hydrolyzable tannins from the fruits of Terminalia chebula Retz and their α-glucosidase inhibitory activities

Lee, Dong Young,Kim, Hyun Woo,Yang, Heejung,Sung, Sang Hyun

, p. 109 - 116 (2017)

Nine hydrolyzable tannins, including three previously unknown and six artifacts, were isolated, together with thirty-nine known ones, from the fruits of Terminalia chebula Retz. (Combretaceae). They were identified as 1,2,3-tri-O-galloyl-6-O-cinnamoyl-β-D

Purification and characterization of tannase and tannase gene from Enterobacter sp.

Sharma, Kanti Prakash,John

, p. 240 - 244 (2011)

Tannase of Enterobacter sp. was purified and characterized at molecular level. It was found to be 90 kDa in molecular weight. The purified enzyme showed maximum activity at 40 °C. The enzyme was also found to be active in acidic range of pH. The nucleotide and amino acid sequence of tannase exhibited resemblance with the other reported tannase sequences of bacteria, fungi and plants. Probably, this is the first report of tannase gene in Enterobacter sp. The investigation suggests that the purified enzyme can be useful to synthesize molecules of pharmaceutical interest. In addition to above, the enzyme tannase and the organism itself can also be employed to protect grazing animals and environment against the toxic effects caused by tannins in them.

Polyphenols in Ammania auriculata: Structures, antioxidative activity and cytotoxicity

Nawwar,Youb,El-Raey,Zaghloul,Hashem,Mostafa,Eldahshan,Werner,Becker,Haertel,Lindequist,Linscheid

, p. 860 - 864 (2014)

Chemical and biological investigations of the extract of Ammania auriculata (Lytheraceae) resulted in the identification of eight polyphenols (1 - 8) for the first time from this plant, including the gallotannin, 2,3,6-tri-O-galloyl-(α,β)-4Csu

MYRICATIN, A GALLOYL FLAVANONOL SULFATE AND PRODELPHINIDIN GALLATES FROM MYRICA RUBRA

Nonaka, Gen-Ichiro,Muta, Makiko,Nishioka, Itsuo

, p. 237 - 242 (1983)

An investigation of the bark of Myrica rubra has led to the isolation and characterization of myricatin (a galloyl flavanonol sulfate) and four new galloyl prodelphinidin dimers, together with gallic acid, (+/-)-gallocatechin and 3-O-galloyl-(-)-epicatechin.Evidence for the structures of these compounds was obtained from analyses of 1H AND 13C NMR spectra, and from hydrolytic studies.Key Word - Myrica rubra; Myricaceae; myricatin; galloyl flavanonol sulfate; prodelphinidin gallates; tannins.

Anthocyanin stability and recovery: Implications for the analysis of clinical and experimental samples

Woodward, Gary,Kroon, Paul,Cassidy, Aedin,Kay, Colin

, p. 5271 - 5278 (2009)

The proportion of ingested anthocyanins to reach the systemic circulation is reported to be a small percentage of their ingested dose. This may be due to physiochemical degradation in vivo or following routine sample treatment. Therefore, this study aimed

Hydrolyzed tannins from Geranium pusillum

Kobakhidze,Alaniya

, p. 262 - 264 (2003)

The polyphenolic compound 1-O-galloyl-3,6-hexahydroxybiphenyl-D- galactopyranoside (pusilagin) was isolated from the aerial part. The tannin structure was established using acid hydrolysis and IR, PMR, and 13C NMR spectral methods.

Solvent-free enzymatic synthesis of 1,2-dipalmitoylgalloylglycerol: Characterization and optimization of reaction condition

Zhang, Siyu,Hyatt, Joseph R.,Akoh, Casimir C.

, (2021)

A novel diacylglycerol-based galloyl structured lipid, 1,2-dipalmitoylgalloylglycerol (DPGG), was synthesized using the enzymatic transesterification of propyl gallate (PG) and tripalmitin under solvent-free condition. An immobilized and commercially available food-grade Candida antarctica lipase B, Lipozyme 435, was used as the biocatalyst. The reaction variables that affect the yield of DPGG were optimized using a 33 full factorial design. At 70 °C, DPGG was obtained at a yield of 33.0 ± 2.0% with PG conversion at 44.8 ± 1.8% when the following condition was used: 25 substrate molar ratio of tripalmitin to PG, 120 h reaction time, and 25% enzyme load relative to the total substrate weight. The structure of reaction product was elucidated using Fourier-transform infrared spectroscopy (FT-IR), electrospray ionization high-resolution accurate-mass tandem mass spectrometry (ESI-HRAM-MS/MS), and 1D and 2D nuclear magnetic resonance spectroscopy (NMR). The effects of different lipases and galloyl donors/acceptors on the transesterification were also investigated.

-

Nierenstein

, p. 630 (1910)

-

Enzymatic synthesis of gallic acid from tannic acid with an inducible hydrolase of Enterobacter spp

Sharma, Kanti Prakash,John,Goswami, Pawas,Soni, Manish

, p. 177 - 184 (2017)

Gallic acid acts as a precursor molecule to synthesize various tannin molecules. These are plant polyphenols and were proved to be good anti-oxidant, anti-cancerous, anti-inflammatory, anti-microbial compounds. In order to fully exploit prominent biological activities of specific tannins and to develop tannin-based new medicines, it is necessary to obtain their pure preparations with an aim of high yield and specificity. In the present study, gallic acid is synthesized by the hydrolysis of tannic acid using a microbial based transformation process. The microorganism was isolated and identified. The ability of the isolated microorganism to covert tannic acid into gallic acid was determined by HPLC and enzyme production.Highlights The present investigation signifies the role of Enterobacter spp. in various processes: ?To synthesize gallic acid (a precursor for food oxidant such as propyl gallate) and a bacteriostatic antibiotic (trimethoprim). ?To protect the environment from tannery’s discharge through the process of biodegradation. ?To reduce the toxicity of tannins in animal feed.

SCYLLO-QUERCITOL GALLATES AND HEXAHYDROXYDIPHENOATES FROM QUERCUS STENOPHYLLA

Nishimura, Hiroaki,Nonaka, Gen-Ichiro,Nishioka, Itsuo

, p. 2599 - 2604 (1986)

Key Word Index - Quercus stenophylla; Fagaceae; scyllo-quercitol; gallotannin; ellagitannin; gallic acid; hexahydroxydiphenic acid.A series of gallotannins and ellagitannins based on a scyllo-quercitol core have been isolated from the bark of Quercus stenophylla.On the basis of chemical and spectroscopic evidence, the structures of the gallotannins have been established as 2-O-, 1,2-di-O-, 1,2,3-tri-O-, 1,2,3,4-tetra-O- and 1,2,3,4,5-penta-O-galloyl-scyllo-quercitols, and the ellagitannins as 1,5-di-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-scyllo-quercitol and 1,4-(or 4,5)-di-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-scyllo-quercitol.

A novel adduct of ECG fused to piceid and four new dimeric stilbene glycosides from: Polygonum cuspidatum

Yang, Ya-Nan,Li, Fu-Shuang,Liu, Fu,Feng, Zi-Ming,Jiang, Jian-Shuang,Zhang, Pei-Cheng

, p. 60741 - 60748 (2016)

Polyflavanostilbene B (1), an unusual adduct of epicatechin-3-O-gallate fused to piceid through a carbon-carbon bond, four new dimeric stilbene glycosides (2-5), three new stilbene glucosides (6-8), one new flavan glucoside (9), and six known compounds were isolated from the rhizome of Polygonum cuspidatum. The structures of these compounds were elucidated using spectroscopic data, including electronic circular dichroism (ECD) and Rh2(OCOCF3)4-induced CD spectra. All of the compounds were screened for their inhibitory activity against α-glucosidase using acarbose as a positive control (IC50 = 385 μM), and strong inhibitory activity against α-glucosidase was observed for compound 8 (IC50 = 3.04 μM).

Anti-inflammatory isocoumarins from the bark of Fraxinus chinensis subsp. rhynchophylla

Lee, Beom Zoo,Kim, Chan-Sik,Jeong, Soon-Kyu,Lee, Sulhae,Lee, Ik Soo,Hong, KwangWon

, p. 4380 - 4387 (2021)

A new isocoumarin (1) named fraxicoumarin was isolated from the bark of Fraxinus chinensis subsp. rhynchophylla along with three known compounds (2–4). The structure of the new compound was established by extensive spectroscopic studies and chemical evidence. The anti-inflammatory effects of the isolated compounds (1–4) on lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells were evaluated in?vitro. Of the compounds tested, compounds 1 and 3 inhibited LPS-induced nitric oxide (NO) production in RAW 264.7 cells. Consistent with these findings, they also suppressed LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein level in RAW 264.7 cells.

Diarylheptanoid sulfates and related compounds from myrica rubra bark

Yoshimura, Morio,Yamakami, Saori,Amakura, Yoshiaki,Yoshida, Takashi

, p. 1798 - 1802 (2012)

Three new diarylheptanoids, myricanol 11-sulfate (1), juglanin B 11-sulfate (2), and myricanone 5-O-(6′-O-galloyl)glucoside (3), were isolated from the bark of Myrica rubra. Compounds 1 and 2 were characterized as diarylheptanoid sulfates on the basis of spectroscopic analyses. The antioxidative activities of the fractionated extracts and isolated compounds were estimated by the oxygen radical absorbance capacity (ORAC) and superoxide dismutase (SOD)-like activity assays. The major isolate, myricitrin (4), displayed a high ORAC value and moderate SOD-like activity (13 198 μmol TE (Trolox equivalent)/g and IC50 127.5 μg/mL, respectively), which might explain the potent antioxidative activity of this material.

New ellagitannin and galloyl esters of phenolic glycosides from sapwood of Quercus mongolica var. crispula (Japanese oak)

Omar, Mohamed,Matsuo, Yosuke,Maeda, Hajime,Saito, Yoshinori,Tanaka, Takashi

, p. 486 - 490 (2013)

Two novel glycosides, 4,5-dimethoxy-3-hydroxyphenol 1-O-β-(6′-O- galloyl)-glucopyranoside (1) and (+)-2α-O-galloyl lyoniresinol 3α-O-β-D-xylopyranoside (2), as well as a novel ellagitannin named epiquisqualin B (3), were isolated from sapwood of Quercus mongolica var. crispula along with 19 known phenolic compounds. The structures of the novel compounds were elucidated on the basis of chemical and spectroscopic investigation. Compound 2 is the first example of a lignan galloyl ester, and 3 is the oxidation product of vescalagin, which is the major ellagitannin of this plant.

Tamarixellagic acid, an ellagitannin from the galls of Tamarix aphylla

Nawwar,Hussein,Buddrus,Linscheid

, p. 1349 - 1354 (1994)

-

ISOLATION OF NORBERGENIN FROM SAXIFRAGA STOLONIFERA

Taneyama, Masatoshi,Yoshida, Seiichi,Kobayashi, Michio,Hasegawa, Masao

, p. 1053 - 1054 (1983)

Key Word Index - Saxifraga stolonifera; Saxifragaceae; desmethylbergenin; norbergenin; bergenin; tri-O-methyl-norbergenin. Norbergenin, a C-glucoside, was isolated from Saxifraga stolonifera and its structure assigned as 2β-D-glucopyranosylgallic acid δ-lactone.

Tannins of tamaricaceous plants. III. New dimeric hydrolyzable tannins from Reaumuria hirtella

Yoshida,Ahmed,Okuda

, p. 672 - 679 (1993)

Four new dimeric hydrolyzable tannins, hirtellins C, D, E and F, besides previously reported hirtellins A and B, have been isolated from the leaf extract of Reaumuria hirtella Jaub. et Sp. (Tamaricaceae). Macrocyclic structures, 1 and 12, having both dehydrodigalloyl (DHDG) and isodehydrodigalloyl (isoDHDG) groups as the connecting units between monomers, were respectively assigned for hirtellin C and F, based on chemical methods, two-dimensional nuclear magnetic resonance measurement and other spectroscopic analyses. Hirtellin D (7) was characterized as an isomer of hirtellin F (12). Hirtellin E (15), having a dehydrotrigalloyl (hellinoyl) group, was characterized as an analog of hirtellin B.

Barth

, p. 1484 Anm. (1875)

Analysis of phenolic compounds in health care products by low-pressure liquid-chromatography with monolithic column and chemiluminescent detection

Ballesta-Claver,Valencia,Capitan-Vallvey

, p. 44 - 53 (2011)

This paper presents a new application for monolithic columns with low-pressure chromatographic separation using an flow injection analysis configuration with chemiluminescent detection for the determination of a mixture of phenolic compounds: phloroglucinol, 2,4-dihydroxybenzoic acid, salicylic acid, methyl paraben and n-propyl gallate. The procedure consists of the separation of these compounds on a reverse-phase ultra-short monolithic column with pH 3.0 acetate buffer and 5% acetonitrile as carrier phase. The detection is based on a chemiluminescence measurement coming from Ce(IV) - Rhodamine 6G chemistry with the incorporation of two different chemiluminescent chemical conditions in the chromatographic setup in order to enhance the sensitivity for the different phenolic compounds. All separation and detection variables were optimized to propose a determination method. The analysis is performed in 280 s, with the sampling frequency being some 13 h-1. The calibration function is a double reciprocal function obtaining good results within two orders of magnitude. The limits of detection were 8.8 × 10-8 M (phloroglucinol), 2.7 × 10-8 M (2,4-dihydroxybenzoic acid); 2.3 × 10-8 M (salicylic acid); 5.2 × 10-8 M (methyl paraben) and 4.1 × 10-6 M (n-propyl gallate), and the relative standard deviations at a medium level of the linear range were 4.4% (phloroglucinol), 2.8% (2,4-dihydroxybenzoic acid), 5.2% (salicylic acid), 3.6% (methyl paraben) and 6.8% (n-propyl gallate). The method was applied and validated satisfactorily for the determination of these compounds in healthcare products, comparing the results against an HPLC reference method. Copyright

Fatty acid synthase inhibitors from Geum japonicum Thunb. var. chinense

Liu, Hongwei,Li, Jiankuan,Zhao, Wenhua,Bao, Li,Song, Xiaohong,Xia, Ying,Wang, Xue,Zhang, Chao,Wang, Xiaozhu,Yao, Xinsheng,Li, Ming

, p. 402 - 410 (2009)

Bioassay-guided fractionation of the MeOH extract of Geum japonicum THUNB. var. chinense using the fatty acid synthase inhibition assay led to the isolation of a new dimeric ellagitannin, gemin G (1), together with six known compounds, gemin A (2), casuar

Study on in Vitro Preparation and Taste Properties of N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols

Han, Zisheng,Ho, Chi-Tang,Jiang, Zongde,Lai, Guoping,Qin, Chunyin,Wan, Xiaochun,Wen, Mingchun,Zhai, Xiaoting,Zhang, Hui,Zhang, Liang

, (2022/04/07)

N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) were prepared by an in vitro model reaction, and the taste thresholds of EPSFs and their dose-over-threshold factors in large-leaf yellow tea (LYT) were investigated. The effects of initial reactant

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