Octyl Gallate

HCID 61253

Basic information

CAS
1034-01-1
Standard SMILES
CCCCCCCCOC(=O)c1cc(O)c(O)c(O)c1
InChIKey
NRPKURNSADTHLJ-UHFFFAOYSA-N
Molecular formula
C15H22O5
Average molar mass
282.33 g/mol
Monoisotopic mass
282.1467238

Overview

Octyl gallate is a gallate ester obtained by condensation of the carboxy group of gallic acid with the hydroxy group of octanol. It has a role as a hypoglycemic agent, a plant metabolite and a food antioxidant.

Names & identifiers

Preferred name
Octyl Gallate
IUPAC
octyl 3,4,5-trihydroxybenzoate
English name
Octyl gallate
Molecular formula
C15H22O5
Molecular weight
282.33

Names & synonyms

Octyl gallate1034-01-1Octyl 3,4,5-trihydroxybenzoaten-Octyl gallateProgallin OStabilizer GA 8Gallic acid, octyl esterGallic acid octyl esterBENZOIC ACID, 3,4,5-TRIHYDROXY-, OCTYL ESTEROktylester kyseliny galloveDTXSID4040713n-Octyl ester of 3,4,5-trihydroxybenzoic acid
Show more names
Stabilizer GA-8OCTYLGALLATE(RG)Gallic acid octyln-OctylGallate>Octyl gallate CRSn-Octyl gallate, 98+%
DTXCID2020713E311NSC-97419079IIA2811INS NO.311PPC-17CHEBI:83631INS-311

Database identifiers

CAS
1034-01-1
PubChem CID
61253
DTXSID
DTXSID4040713
ChEMBL
CHEMBL277346
ChEBI
CHEBI:83631
UNII
079IIA2811
EC Number
213-853-0
Nikkaji
J12.253J

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
87 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
9
Heavy atoms
20

Experimental & physicochemical properties

LogP · 2 items

3.66

3.66

Food AdditivesANTIOXIDANT -> FDA Substance added to food
Solubility · 2 items

Insoluble in water, freely soluble in ethanol, ether and propane-1,2-diol

0.036 mg/mL at 20 °C

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point · 2 items

Between 99 °C and 102 °C after drying at 90 °C for six hours

94 - 95 °C

Physical Description · 2 items

White to creamy-white odourless solid

Solid

Physicochemical properties

Melting point
101 · 101-104 °C(lit.)
Boiling point
262.5 °C · 262.5°C (estimate)
Density
1.0984 · 1.0984 (rough estimate)
refractive index
1.62 · 1.6200 (estimate)
storage temp.
30 °C · Store below +30°C.
solubility
2.5 %, · soluble2.5%, clear, colorless (AcOH (MEOH))

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 13.4% (11 of 82) of reports.

Warning

H302 (86.6%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 3 items

Chemical: Benzoic acid, 3,4,5-trihydroxy-, octyl ester

Regulation (EC) No 1333/2008 (amended)

Octyl Gallate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and Categories · 3 items

Acute Tox. 4 (86.6%)

Acute toxicity - category 4

Acute Tox. 4 *

Toxicology

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
1
tsca
TSCA listed
rtecs
LW8225000
hs_code
2918 29 00
Toxicity
LD50 orally in Rabbit: 1960 mg/kg
risk_code
22-43

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances capable of inhibiting, retarding or arresting the process of fermentation, acidification or other deterioration of foods.
Cellular LocationsMembrane

Uses & manufacturing

Use Classification · 2 items

Food additives

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

General Manufacturing InformationBenzoic acid, 3,4,5-trihydroxy-, octyl ester: ACTIVE
Applications · 6 items

DescriptionOctyl 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.

DescriptionDuring 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.

UsesUsed in treatment of alcohol dependence.

UsesOctyl gallate is an antioxidant that is used as a preservation agent in a wide variety of foods, oils, and cosmetics.

UsesOctyl gallate is an antioxidant for use in cosmetic and pharmaceutical products and in food products, such as margarine and peanut butter.

General DescriptionOctyl 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)

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
上海赫文斯化工有限公司15721252604 17321035817 · [email protected]

Additional notes

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

Related reactions

2 records

Compound notes

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