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1034-01-1

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1034-01-1 Usage

Description

Different sources of media describe the Description of 1034-01-1 differently. You can refer to the following data:
1. Octyl gallate is the ester formed by 1-octanol and gallic acid. It can be used as an antioxidant and preservative to be supplemented to the food. It has been demonstrated to be an effective fungicide being capable of inhibiting the growth of S. cerevisiae and Z. bailii as it can inhibit the fluidity of the cell membrane through acting as a nonionic surface-active agent. It is also capable of killing both DNA and RNA viruses with a relatively moderate cytotoxicity. For example, it has the potential to treat influenza. Octyl gallate also has certain bactericidal activity, being capable of treating the infections associated with enterococci.
2. During the 1940s, propyl gallate and several other alkyl gallates were allowed for use in foods in a number of countries. Since gallic acid contains three phenolic hydroxyl groups, it is a rather potent antioxidant; however, the propyl ester has a significant degree of water solubility. As a consequence, propyl gallate tends to partition into any water phase which may be present and to complex with iron salts to give bluish black colors. Also, its relatively poor resistance to heat degradation makes it ineffective for baking and frying applications. The higher alkyl gallates (butyl and octyl) are more fat soluble.

References

[1]Ken-Ichi, Fujita, and K. Isao. "Antifungal activity of octyl gallate. " International Journal of Food Microbiology 79.3(2002):1 [2]Gutiérrez-Fernández, J, et al. "Antimicrobial activity of binary combinations of natural and synthetic phenolic antioxidants against Enterococcus faecalis. " Journal of Dairy Science 96.8(2013):4912-20.93. [3] Yamasaki, H, et al. "Antiviral effect of octyl gallate against influenza and other RNA viruses. " International Journal of Molecular Medicine 19.4(2007): 685-688.

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 1034-01-1 differently. You can refer to the following data:
1. Used in treatment of alcohol dependence.
2. Octyl gallate is an antioxidant that is used as a preservation agent in a wide variety of foods, oils, and cosmetics.
3. Octyl gallate is an antioxidant for use in cosmetic and pharmaceutical products and in food products, such as margarine and peanut butter.

Definition

ChEBI: A gallate ester obtained by condensation of the carboxy group of gallic acid with the hydroxy group of octanol.

General Description

Octyl gallate is an ester of gallic acid which is generally used as an antioxidant in food and pharmaceutical industries. It can act against the oxidative damage caused by reactive oxygen species (ROS) in the form of hydroxyl radicals or hydrogen peroxides, and reactive sulfur species (RSS)

Contact allergens

Octyl gallate, a gallate ester (E 311), is an antioxidant added to food and cosmetics to prevent oxidation of unsaturated fatty acids. Cases were sparsely reported in food industry or from lipsticks. Patch tests are frequently irritant.

Safety Profile

A poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 1034-01-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,3 and 4 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1034-01:
(6*1)+(5*0)+(4*3)+(3*4)+(2*0)+(1*1)=31
31 % 10 = 1
So 1034-01-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H22O5/c1-2-3-4-5-6-7-8-20-15(19)11-9-12(16)14(18)13(17)10-11/h9-10,16-18H,2-8H2,1H3

1034-01-1 Well-known Company Product Price

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

  • (L06081)  n-Octyl gallate, 98+%   

  • 1034-01-1

  • 25g

  • 306.0CNY

  • Detail
  • Alfa Aesar

  • (L06081)  n-Octyl gallate, 98+%   

  • 1034-01-1

  • 100g

  • 1004.0CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000368)  Octylgallate  European Pharmacopoeia (EP) Reference Standard

  • 1034-01-1

  • Y0000368

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (06717)  Octylgallate  analytical reference material

  • 1034-01-1

  • 06717-500MG

  • 965.25CNY

  • Detail

1034-01-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name octyl gallate

1.2 Other means of identification

Product number -
Other names octyl 3,4,5-trihydroxybenzoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives
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:1034-01-1 SDS

1034-01-1Synthetic route

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%
octanol
111-87-5

octanol

Ethyl gallate
831-61-8

Ethyl gallate

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In toluene Reflux;94.1%
octanol
111-87-5

octanol

methyl galloate
99-24-1

methyl galloate

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In toluene Solvent; Reflux;93.9%
octanol
111-87-5

octanol

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

isopropyl 3,4,5-trihydroxybenzoate

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In chlorobenzene Reflux;91.9%
octanol
111-87-5

octanol

n-butyl gallate
1083-41-6

n-butyl gallate

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In 5,5-dimethyl-1,3-cyclohexadiene Reflux;90.1%
octanol
111-87-5

octanol

Propyl gallate
121-79-9

Propyl gallate

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In 5,5-dimethyl-1,3-cyclohexadiene Reflux;89.9%
octanol
111-87-5

octanol

3,4,5-trihydroxybenzoyl chloride
35388-10-4

3,4,5-trihydroxybenzoyl chloride

Octyl gallate
1034-01-1

Octyl gallate

3.4.5-tribenzyloxy-benzoic acid octyl ester

3.4.5-tribenzyloxy-benzoic acid octyl ester

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With palladium on activated charcoal; ethanol Hydrogenation;
octanol
111-87-5

octanol

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
With sulfuric acid
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Octyl gallate
1034-01-1

Octyl gallate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / 35 - 65 °C
2: tris(pentafluorophenyl)borate / 5,5-dimethyl-1,3-cyclohexadiene / Reflux
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / 35 - 65 °C
2: tris(pentafluorophenyl)borate / chlorobenzene / Reflux
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / 35 - 65 °C
2: tris(pentafluorophenyl)borate / toluene / Reflux
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / 35 °C / Reflux; Large scale
2: tris(pentafluorophenyl)borate / toluene / Reflux
View Scheme
Octyl gallate
1034-01-1

Octyl gallate

triphenylantimony dichloride
594-31-0, 34716-91-1, 20265-29-6

triphenylantimony dichloride

C33H35O5Sb

C33H35O5Sb

Conditions
ConditionsYield
In tetrahydrofuran73%
Octyl gallate
1034-01-1

Octyl gallate

acetic anhydride
108-24-7

acetic anhydride

octyl-3-acetoxy-4,5-dihydroxybenzoate

octyl-3-acetoxy-4,5-dihydroxybenzoate

Conditions
ConditionsYield
With pyridine at 100℃; for 168h;56%
3-methocycatechol
934-00-9

3-methocycatechol

Octyl gallate
1034-01-1

Octyl gallate

octyl 3,4,6-trihydroxy-2-methoxy-5-oxo-5H-benzo[7]annulene-8-carboxylate
1416324-80-5

octyl 3,4,6-trihydroxy-2-methoxy-5-oxo-5H-benzo[7]annulene-8-carboxylate

Conditions
ConditionsYield
With dihydrogen peroxide; horseradish peroxidase In aq. phosphate buffer; acetone pH=5;52.7%
Glyoxal
131543-46-9

Glyoxal

Octyl gallate
1034-01-1

Octyl gallate

C17H24O7

C17H24O7

Conditions
ConditionsYield
In aq. phosphate buffer at 80℃; for 2h; pH=7;8.4%
acetamide
60-35-5

acetamide

Octyl gallate
1034-01-1

Octyl gallate

Glyoxilic acid
298-12-4

Glyoxilic acid

2-(Acetylamino-carboxy-methyl)-3,4,5-trihydroxy-benzoic acid octyl ester
68802-30-2

2-(Acetylamino-carboxy-methyl)-3,4,5-trihydroxy-benzoic acid octyl ester

Conditions
ConditionsYield
(i) AcOH, (ii) HCl, /BRN= 2132305/; Multistep reaction;
Octyl gallate
1034-01-1

Octyl gallate

octyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-O-isopropylidene-benzoate
1329454-54-7

octyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-O-isopropylidene-benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2: boron trifluoride diethyl etherate / dichloromethane
View Scheme
Octyl gallate
1034-01-1

Octyl gallate

octyl 3-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4,5-O-isopropylidene-benzoate
1329454-89-8

octyl 3-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4,5-O-isopropylidene-benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2: boron trifluoride diethyl etherate / dichloromethane
View Scheme
Octyl gallate
1034-01-1

Octyl gallate

octyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-dihydroxybenzoate
1329454-65-0

octyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)-4,5-dihydroxybenzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2: boron trifluoride diethyl etherate / dichloromethane
3: trifluoroacetic acid / 24 h / 20 °C
View Scheme
Octyl gallate
1034-01-1

Octyl gallate

octyl 3-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4,5-dihydroxybenzoate
1329454-93-4

octyl 3-O-(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4,5-dihydroxybenzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2: boron trifluoride diethyl etherate / dichloromethane
3: trifluoroacetic acid / 24 h / 20 °C
View Scheme
Octyl gallate
1034-01-1

Octyl gallate

octyl 3-O-(β-D-glucopyranosyl)-4,5-dihydroxybenzoate
1329454-76-3

octyl 3-O-(β-D-glucopyranosyl)-4,5-dihydroxybenzoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2.1: boron trifluoride diethyl etherate / dichloromethane
3.1: trifluoroacetic acid / 24 h / 20 °C
4.1: methanol; sodium carbonate / 1 h
4.2: pH 7
View Scheme
Octyl gallate
1034-01-1

Octyl gallate

octyl 3-O-(β-D-glucopyranosyluronate)-4,5-dihydroxybenzoate
1329454-99-0

octyl 3-O-(β-D-glucopyranosyluronate)-4,5-dihydroxybenzoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: camphor-10-sulfonic acid / chloroform / 16 h / 60 °C
2.1: boron trifluoride diethyl etherate / dichloromethane
3.1: trifluoroacetic acid / 24 h / 20 °C
4.1: methanol; sodium carbonate / 1 h
4.2: pH 7
View Scheme
Octyl gallate
1034-01-1

Octyl gallate

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

C18H26O5
1329454-42-3

C18H26O5

Conditions
ConditionsYield
With camphor-10-sulfonic acid In chloroform at 60℃; for 16h;
Octyl gallate
1034-01-1

Octyl gallate

benzene-1,2-diol
120-80-9

benzene-1,2-diol

C20H24O6
1283016-29-4

C20H24O6

Conditions
ConditionsYield
In ethyl acetate at 20℃; pH=5; phthalate buffer;
With laccase from Trametes versicolor In ethyl acetate at 20℃; for 48h; pH=5;1.26 g
Octyl gallate
1034-01-1

Octyl gallate

C19H26O9

C19H26O9

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. phosphate buffer / 2 h / 80 °C / pH 7
2: aq. phosphate buffer / 2 h / 100 °C / pH 7
View Scheme

1034-01-1Related news

Antiviral effect of Octyl gallate (cas 1034-01-1) against DNA and RNA viruses07/29/2019

The effects of gallic acid (3,4,5-trihydroxybenzoic acid) and its alkyl esters on virus growth and virion infectivity were examined. All the compounds tested showed an inhibitory effect on the growth of herpes simplex virus type 1 (HSV-1) in HEp-2 or Vero cells. The antiviral activity of gallic ...detailed

Evaluation of antifungal properties of Octyl gallate (cas 1034-01-1) and its synergy with cinnamaldehyde07/27/2019

The objective of this study was to investigate the possibility of using octyl gallate alone or with organic biocides as a preservative against wood decay fungi. Antifungal activities of three antioxidants, propyl gallate, octyl gallate and butylated hydroxyltoluene (BHT) were tested against four...detailed

Octyl gallate (cas 1034-01-1) and gallic acid isolated from Terminalia bellarica regulates normal cell cycle in human breast cancer cell lines07/25/2019

Herbal medicines stand unique and effective in treating human diseases. Terminalia bellarica (T. bellarica) is a potent medicinal herb, with a wide range of pharmacological activities. The present study was aimed to evaluate the effect of octyl gallate (OG) and gallic acid (GA) isolated from met...detailed

Octyl gallate (cas 1034-01-1) reduces ATP levels and Ki67 expression leading HepG2 cells to cell cycle arrest and mitochondria-mediated apoptosis07/23/2019

Octyl gallate (OG) is an antioxidant that has shown anti-tumor, anti-diabetic and anti-amyloidogenic activities. Mitochondria play an important role in hepatocellular carcinoma, mainly by maintaining accelerated cellular proliferation through the production of ATP. Thus, the mitochondria may be ...detailed

1034-01-1Relevant articles and documents

Antifungal activity of octyl gallate: Structural criteria and mode of action

Kubo, Isao,Xiao, Ping,Fujita, Ken'ichi

, p. 347 - 350 (2001)

Octyl gallate (3,4,5-trihydroxybenzoate) was found to possess antifungal activity against Saccharomyces cerevisiae and Zygosaccharomyces bailii, in addition to its potent antioxidant activity. Catechol moiety is essential to elicit this activity. The primary fungicidal activity of octyl gallate comes from its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl chain is not a major contributor but plays an important role in eliciting the activity.

Molecular design of antibrowning agents

Kubo, Isao,Kinst-Hori, Ikuyo,Kubo, Yumi,Yamagiwa, Yoshiro,Kamikawa, Tadao,Haraguchi, Hiroyuki

, p. 1393 - 1399 (2000)

Tyrosinase inhibitory and antioxidant activity of gallic acid and its series of alkyl chain esters were investigated. All inhibited the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by mushroom tyrosinase. However, gallic acid and its short alkyl chain esters were oxidized as substrates yielding the colored oxidation products. In contrast, the long alkyl chain esters inhibited the enzyme activity without being oxidized. This indicates that the carbon chain length is associated with their tyrosinase inhibitory activity, presumably by interacting with the hydrophobic protein pocket in the enzyme. On the other hand, the esters, regardless their carbon chain length, showed potent scavenging activity on the autoxidation of linoleic acid and 1,1-diphenyl-2-p-picryhydrazyl (DPPH) radical, suggesting that the alkyl chain length is not related to the activity. The effects of side-chain length of gallates in relation to their antibrowning activity are studied.

A preparation method of electronic grade gallic octyl ester

-

, (2019/03/31)

The present invention provides a kind of electronic grade gallic octyl ester of preparation method, which belongs to the technical field of organic synthesis. The gallic acid dissolved in alcohol, then drop adds the chlorination [...], then adding aromatic hydrocarbon solvent, a catalytic amount of B (C6F5) 3 and octanol, moiety will be distillation after the exchange, getting the gallic octyl ester. This method avoids the use of heavy metal catalyst, high yield, low cost, and is suitable for industrial scale production, the ester exchange after the end of the added metal ion adsorbent after the metal ion adsorption, distillation electronic level of gallic octyl ester.

Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution

Bergquist, Bridget L.,Jefferson, Kaelyn G.,Kintz, Hailey N.,Barber, Amorette E.,Yeagley, Andrew A.

supporting information, p. 51 - 55 (2018/05/04)

Commercially utilized parabens are employed for their antimicrobial properties, but a weak binding to the estrogen receptor alpha (ERα) may lead to breast cancer in some applications. Modification of the paraben scaffold should allow for a disconnection of these observed properties. Toward this goal, various 3,5-substituted parabens were synthesized and assessed for antimicrobial properties against S. aureus as well as competitive binding to the ERα. The minimum inhibitory concentration assay confirmed retention of antimicrobial activity in many of these derivatives, while all compounds exhibited decreased xenoestrogen activity as determined by a combination of competitive enzyme linked immunosorbent assay (ELISA), proliferation, and estrogen receptor binding assay. Thus, these changes to the paraben scaffold have led to a multitude of paraben derivatives with antimicrobial properties up to 16 times more active than the parent paraben and that are devoid or significantly diminished of potential breast cancer causing properties.

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