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Gluconic Acid

HCID 10690
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
133-42-6
Standard-SMILES
O=C(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChIKey
RGHNJXZEOKUKBD-SQOUGZDYSA-N
Summenformel
C6H12O7
Durchschnittliche Molmasse
196,16 g/mol
Monoisotopische Masse
196,05830272

Überblick

D-gluconic acid is a gluconic acid having D-configuration. It has a role as a chelator and a Penicillium metabolite. It is a conjugate acid of a D-gluconate. It is an enantiomer of a L-gluconic acid.

Namen und Bezeichner

Bevorzugter Name
Gluconic Acid
IUPAC
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid

Namen und Synonyme

gluconic acidD-gluconic acid526-95-4dextronic acidmaltonic acidGlycogenic acid(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acidGlosantoPentahydroxycaproic acidD-Gluco-hexonic acidDTXSID8027169R4R8J0Q44B
Weitere Namen anzeigen
DTXCID307169INS NO.574DTXSID8042000CHEBI:33198INS-574E-574NSC-77381NSC77381

Datenbank-Bezeichner

CAS
133-42-6、526-95-4
PubChem CID
10690
DTXSID
DTXSID8042000
ChEMBL
CHEMBL464345
ChEBI
CHEBI:33198
UNII
R4R8J0Q44B
EC Number
208-401-4
Nikkaji
J3.286G

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-3,4
Polarare Oberfläche (TPSA)
138 Ų
H-Brücken-Donoren
6
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
5
Schwere Atome
13
Formalladung
0
Komplexität
170

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 2 Einträge

Cosmetic ingredients (Gluconic Acid) -> CIR (Cosmetic Ingredient Review)

Humectant; Solvent; Buffering

LogP-1.87 (estimated)
TasteMILD ACID TASTE
Food AdditivesNUTRIENT SUPPLEMENT -> FDA Substance added to food
Density · 3 Einträge

1.24 @ 25 °C/4 °C

1.23 g/cm³

1.24 @25 °C

Color/Form · 2 Einträge

NEEDLES FROM ETHANOL & ETHER

CRYSTALS

Solubility · 3 Einträge

FREELY SOL IN WATER; SLIGHTLY SOL IN ALC, INSOLUBLE IN ETHER AND MOST OTHER ORGANIC SOLVENTS

316 mg/mL at 25 °C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 33% (257 of 779) of reports.

Warning

H315 (60.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 779 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: D-Gluconic acid

D-Gluconic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of D-Gluconic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 16-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/1957

D-Gluconic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - D-Gluconic acid: Environment tier I assessment
Fire HazardsCombustible.
Hazards Summary · 1 Eintrag

Emergency treatment: Irritants; [HSDB] No significant adverse effects in chronic studies of animals; Reproductive studies negative; No data available on carcinogenicity or inhalation toxicity; [OECD SIDS: Gluconic acid and its derivatives - 2004] 50% aqueous solution: A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]

Chemie und Industrie

Pharmakologische Informationen

PharmacodynamicsUsed as part of electrolyte salts to maintain cation-anion balance in solutions.
Absorption, Distribution and Excretion(99)TCM-LABELED GLUCONATE WAS ACCUMULATED RELATIVELY EARLY IN THE KIDNEY, AND ESP IN THE URINARY TRACT.
Tissue LocationsPlacenta
Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Gluconic Acid

Primary acid in honey; Used in pharmaceutical and food products, for cleaning and pickling metals, as a sequestrant, in paint strippers, and in alkaline rust removers; [Hawley] Used as a chelating agent, high alkalinity bottle cleanser, and finish remover; Used in the tanning and textile industries; [Merck Index] Important intermediate in carbohydrate metabolism in mammals; Used for industrial cleaning, metal surface treatment, textile bleach stabilizing, aluminum processing, and as a chelating agent in cement set retarding, cleaning products, personal care products, pharmaceuticals, and foods; [OECD SIDS: Gluconic acid and its derivatives - 2004]

Aluminum Producing [Category: Industry]

For Gluconic acid (USEPA/OPP Pesticide Code: 000104) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

IN DAIRY INDUST TO PREVENT MILKSTONE; IN BREWERIES TO PREVENT BEERSTONE; LATENT ACID CATALYST FOR ACID COLLOID RESINS, PARTICULARLY IN TEXTILE PRINTING COMPONENT OF MANY CLEANING COMPOUNDS... /GLUCONOLACTONE/

U.S. Imports(1984) 5.44X10+7 g
U.S. Production2023: 10,000,000 - <25,000,000 lb

Zugehörige Reaktionen

34
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 47053
HRID 47053als Produktals Eduktuspto-grants-1979_11
Reaktionsgleichung von HRID 67153
HRID 67153als Eduktuspto-grants-1982_08
Reaktionsgleichung von HRID 232110
HRID 232110als Eduktuspto-grants-1989_07
Reaktionsgleichung von HRID 329913
HRID 329913als Eduktuspto-grants-1990_01
Reaktionsgleichung von HRID 355499
HRID 355499als Eduktuspto-grants-1998_11
Reaktionsgleichung von HRID 373089
HRID 373089als Eduktuspto-grants-1992_11
Reaktionsgleichung von HRID 493899
HRID 493899als Eduktuspto-grants-2009_05
Reaktionsgleichung von HRID 522487
HRID 522487als Produktuspto-grants-2016_05
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Solubility in water, g/100ml at 25 °C: 100 (good)

Melting Point · 4 Einträge

131 °C

113 - 118 °C

131 °C

131 °C

Optical Rotation · 2 Einträge

SPECIFIC OPTICAL ROTATION: -3.49 TO +12.95 DEG @ 25 °C/D (WATER); MUTAROTATORY; SADTLER REFERENCE NUMBER: 8335 (IR, PRISM)

SPECIFIC OPTICAL ROTATION: -6.7 DEG @ 20 °C/D (CONCN= 1 G/100 ML WATER)

Physical Description · 5 Einträge

Dry Powder; Liquid; Liquid; Other Solid

Colourless to light yellow, clear syrupy liquid

Light brown solid; Commercial product is 50% aqueous solution; [Hawley] 50% aqueous solution: Pale yellow liquid; [MSDSonline]

Solid

WHITE CRYSTALLINE POWDER.

EPA Safer Chemical
Chemical: D-Gluconic acid
FIFRA Requirements · 2 Einträge

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Gluconic acid is found on List D. Case No: 4043; Pesticide type: Antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Gluconic acid; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Gluconic acid (and sodium salt) is exempted from the requirement of a tolerance when used as a sequestrant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.

Chemical DangersOn combustion, forms carbon monoxide. Reacts with strong oxidants. The solution in water is a medium strong acid.
Hazard Classes and CategoriesSkin Irrit. 2 (60.6%)

Sicherheit und Schutzausrüstung

Fire FightingUse powder, alcohol-resistant foam, water spray, carbon dioxide.
First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse skin with plenty of water or shower.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth.

Safe StorageSeparated from strong oxidants.
Storage ConditionsMAY BE STORED IN STAINLESS STEEL DRUMS. /COMMERCIAL PRODUCT/
Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 Eintrag

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.

Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly when dispersed.
Allowable Tolerances · 1 Eintrag

Gluconic acid (and sodium salt) is exempted from the requirement of a tolerance when used as a sequestrant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.

Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse local exhaust or breathing protection.
Protective Action Criteria (PAC) · 3 Einträge

18 [mg/m3]

200 [mg/m3]

1200 [mg/m3]

Toxikologische Informationen

Adverse EffectsDermatotoxin - Skin burns.
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Signs and SymptomsRedness.

Regulatorische Informationen

FIFRA Requirements · 2 Einträge

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Gluconic acid is found on List D. Case No: 4043; Pesticide type: Antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Gluconic acid; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Gluconic acid (and sodium salt) is exempted from the requirement of a tolerance when used as a sequestrant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.

Consumer UsesProcessing aids not otherwise specified
Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 5 Einträge

MAY BE PREPARED FROM GLUCOSE BY ELECTROLYTIC OXIDN IN ALKALINE MEDIUM; BY CHEM OXIDN WITH HYPOBROMITES

BY HYDROLYSIS OF ALPHA-D-GLUCOSE WITH BROMINE PLUS H2SO4; BY GAMMA-IRRADIATION OF D-GLUCOSE;

AT PRESENT PRODUCED IN COMMERCIAL QUANTITIES BY FERMENTATIVE OXIDN OF ALDEHYDE GROUP IN GLUCOSE FROM CORN USING ASPERGILLUS NIGER, ASPERGILLUS FUMARICUS, ACETOBACTER ACETI, PENICILLIUM CHRYSOGENUM, & OTHER PENICILLIA.

CANNIZZARO REACTION ON GLUCOSE UNDER ALKALINE CONDITIONS FORMS SORBITOL AND GLUCONIC ACID

For more Methods of Manufacturing (Complete) data for GLUCONIC ACID (6 total), please visit the HSDB record page.

Formulations/Preparations · 2 Einträge

BECAUSE OF DIFFICULTIES OF PREPARING SOLID CRYSTAL PRODUCT, GLUCONIC ACID OF COMMERCE IS 50% AQ SOLN...

GRADES: TECHNICAL, 50% SOLN.

Household Products · 2 Einträge

Information on 24 consumer products that contain D-Gluconic acid in the following categories is provided:

Information on 4 consumer products that contain Gluconic acid in the following categories is provided:

Use Classification · 5 Einträge

EPA Safer Chemical Functional Use Classes -> Chelating Agents;Processing Aids and Additives

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Food additives

Food Additives -> ACID; ACIDITY_REGULATOR; RAISING_AGENT; SEQUESTRANT -> JECFA Functional Classes

Cosmetics -> Humectant; Solvent; Buffering

General Manufacturing Information · 3 Einträge

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

D-Gluconic acid: ACTIVE

IT IS CHIEF ACID IN HONEY.