3D Mol Similar

D-(+)-Glucono-1,5-lactone

: Iupac Name：(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one; CAS No.: 90-80-2; Molecular Weight：178.14000; Modify Date.: 2022-11-29 12:37; Introduction: Delta-Gluconolactone (GDL) is a lactone of the D-gluconate. It is a natural constituent of many foods. It can be found in honey, fruit juices, wine and many-fermented products1-3. It is used as a food additive with the E number E575 used as a sequestrant, an acidifier (it lower the pH and also help preserve the food from deterioration by enzymes and organisms), or a curing, pickling, or leavening agent. GDL has been marketed for use in feta cheese. GDL is neutral, but hydrolyses in water to gluconic acid that is acidic, adding a tangy taste to foods, though it has roughly a third of the sourness of citric acid. It can be used as nutritional supplement in beverage such as in Instant Drinks, Syrups, RTD Tea and Coffee, Sports and Energy Drinks, Waters. View more+

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1. Names and Identifiers

: 1.1 Name; D-(+)-Glucono-1,5-lactone; 1.2 Synonyms; (3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one 1,2,3,4,5-PENTAHYDROXYCAPROIC ACID DELTA-LACTONE Cagliflozin Impurity 8 D(+)-DEXTRONIC ACID DELTA-LACTONE DELTA-GLUCONOLACTONE delta-Gluconolactone in stock GMP Factory DELTA-GLUCURONOLACTONE D-Gluconic acid 1,5-lactone d-gluconic acid d-lactone D-Gluconic acid lactone D-Gluconic acid, Δ-lactone D-Gluconic acid-1,5-lactone D-Glucono-1,5-lactone D-Glucono-d-lactone D-Gluconolactone EINECS 202-016-5 Gluconic acid lactone Glucono Delta Lactone, Glucono Delta Lactone powder Glucono Δ-lactone Gluconolactone - CAS 90-80-2 - Calbiochem MFCD00006647 Δ-Gluconic acid d-lactone Δ-Gluconic acid Δ-lactone Δ-Gluconolactone; View all

1.3 CAS No.: 90-80-2

1.4 CID: 7027

1.5 EINECS(EC#): 202-016-5

1.6 Molecular Formula: C6H10O6 (isomer)

1.7 Inchi: InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1

1.8 InChIkey: PHOQVHQSTUBQQK-SQOUGZDYSA-N

1.9 Canonical Smiles: C(C1C(C(C(C(=O)O1)O)O)O)O

1.10 Isomers Smiles: C([C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O)O)O)O

2. Properties

2.1 Density: 0.6

2.1 Melting point: 160°C (dec.)(lit.)

2.1 Boiling point: 446.4ºC at 760 mmHg

2.1 Refractive index: 63.5 ° (C=10, H2O)

2.1 Flash Point: 192.3ºC

2.1 Precise Quality: 178.04800

2.1 PSA: 107.22000

2.1 logP: -3.01320

2.1 Solubility: 590g/l Hydrolysis

2.2 Appearance: Powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: Powder

2.5 Color/Form: White crystals

2.6 PH: Freshly prepared aqueous solution has pH of 3.6, changing to 2.5 within 2 hours

2.7 pKa: 12.06±0.60(Predicted)

2.8 Water Solubility: H2O: 500 g/L (20 ºC)

2.9 Spectral Properties: Specific optical rotation = +63.5 deg to +6.2 deg at 25 deg C (solvent= water) mutarotatory
SADTLER REFERENCE NUMBER: 5145 (IR, PRISM)
IR: 1588 (Coblentz Society Spectral Collection)
NMR: 10934 (Sadtler Research Laboratories Spectral Collection)

2.10 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 Methods of Manufacturing: 1. Raw calcium gluconate hydrolysis with sulfuric acid, in gluconic acid solution. The calcium sulfate precipitate is removed by filtration, and the solution is refined by barium hydroxide and oxalic acid, and the solution is separated and sedimentated to remove SO42- and Ca2 + in solution. The gluconic acid solution is then further purified by ion exchange resin. Concentrating the solution to 80-85% concentration, adding glucono-delta-lactone seeds, concentrating and crystallizing, and then centrifuging; washing with water; drying to obtain finished product.
2. Calcium gluconate first hydrolysis with sulfuric acid, in gluconic acid solution. The calcium sulfate precipitate is removed by filtration, and the solution is refined by barium hydroxide and oxalic acid, and the solution is separated and sedimentated to remove SO42- and Ca2 + in the solution. The gluconic acid solution is then further purified by ion exchange resin. Concentrating the solution to 80-85 percent, adding gluconic acid δ-lactone seeds, concentrating and crystallizing, centrifugally separating, washing and drying.; View all

3.2 Purification Methods: Crystallise Dglucono-lactone from ethylene glycol monomethyl ether and dry for 1hour at 110o. It can be freed from other sugars via a column of Celite and charcoal (750g of each, 90 x 7.5cm) which is washed with 0.01N formic acid until the pH of the wash is equal to that of the entering acid. The lactone is applied in H2O and eluted with 0.01N formic acid (7L), then eluted with 7.5% EtOH/0.01N formic acid (8L), then 15% EtOH/0.01N formic acid (8L) which removes pentose and isomaltose (the optical rotation of the eluates are used for sugar detection) and finally elution with aqueous formic acid provides glucolactone which is obtained by evaporating or freeze drying. Its solubility in H2O is 60% and 1% in EtOH. A solution in H2O is slightly acidic, and the lactone dissolves in an equivalent of aqueous NaOH to form sodium D-gluconate [527-07-1] M 218.1, m 2002 0 6o(dec), [ ] D 25 +12o (c 10, H2O), pK2 5 3.6. [cf p 553, Smith & Whelan Biochemical Preparations 10 127 1963, Beilstein 3 IV 1255.] D-(+)-Glucono-1,5-lactone Preparation Products And Raw materials Raw materials; View all

3.3 Usage: Geogard(R)Ultra is a synergistic blend of gluconolactone and sodium benzoate. This blend provides broad spectrum protection against product spoilage in a variety of personal care formulations. Product Data Sheet

4. Safety and Handling

4.1 Hazard Codes: Xn; Xi

4.1 Risk Statements: R21

4.1 Safety Statements: S24/25

4.1 Octanol/Water Partition Coefficient: log Kow = -1.98 (est)

4.2 Hazard Declaration: H319

4.2 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.3 RIDADR: NONH for all modes of transport

4.3 Safety Profile: Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

4.4 Caution Statement: P264, P280, P305+P351+P338, P33, P313

4.4 WGK Germany: 3

4.4 RTECS: LZ5184000

4.4 Report: Reported in EPA TSCA Inventory.

4.5 Safety: Hazard Codes:?Xn,Xi
Risk Statements:
R21:? Harmful in contact with skin?
R46:? May cause heritable genetic damage?
R62:? Possible risk of impaired fertility?
R63:? Possible risk of harm to the unborn child?
R36/37:? Irritating to eyes and respiratory system?
Safety Statements:
S25:? Avoid contact with eyes?
S26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
S53:? Avoid exposure - obtain special instruction before use
S24/25:? Avoid contact with skin and eyes?
S36/37:? Wear suitable protective clothing and gloves
WGK Germany: 3
RTECS: LZ5184000
F: 21
Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.; View all

4.6 Specification: ? 1,5-Gluconolactone (CAS NO.90-80-2), its Synonyms are D-Gluconic acid delta-lactone ; D-Gluconic acid lactone ; D-Gluconic delta-lactone ; D-Glucono-1,5-lactone ; D-delta-Gluconolactone ; Deltagluconolactone ; Gluconic acid lactone (6CI) ; Gluconic delta-lactone ; Glucono delta lactone ; Glucono delta-lactone ; Gluconolactone ; delta-Gluconolactone ; beta-Glucono-1,5-lactone .

4.7 Toxicity

???

uns-mic-uns 5?mmol/L

???

AMICCW ?? Archives of Microbiology. 109 (1976),157.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

90-80-2Total: 3 Synthesis Route

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Literatures:
Helvetica Chimica Acta, , vol. 83, # 12 p. 3211 - 3228
Yield: null

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526-95-4 187 Suppliers

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Literatures:
Arjona; Guerra-Balcazar; Trejo; Ledesma-Garcia; Arriaga New Journal of Chemistry, 2012 , vol. 36, # 12 p. 2555 - 2561
Yield: null

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Literatures:
Andrews, Mark A.; Gould, George L.; Klaeren, Stephen A. Journal of Organic Chemistry, 1989 , vol. 54, # 22 p. 5257 - 5264
Yield: null

8. Other Information

8.0 Usage: Glucono delta-lactone?(GDL) is a kind of excellent multifunctional food additive. It is mainly used as protein coagulant, acidifier, pickling, or?leavening agent. expander, preservative, seasonings, sequestrant, chelating agent, color-preserver, etc. it is widely applied to food, daily chemical industry, pharmaceuticals, cosmetics. Plastic and resinous modification, electrode position and polish, metal-surface cleaning and organic synthesis.

8.1 Storage Conditions: 1. Raw calcium gluconate hydrolysis with sulfuric acid, in gluconic acid solution. The calcium sulfate precipitate is removed by filtration, and the solution is refined by barium hydroxide and oxalic acid, and the solution is separated and sedimentated to remove SO42- and Ca2 + in solution. The gluconic acid solution is then further purified by ion exchange resin. Concentrating the solution to 80-85% concentration, adding glucono-delta-lactone seeds, concentrating and crystallizing, and then centrifuging; washing with water; drying to obtain finished product.
2. Calcium gluconate first hydrolysis with sulfuric acid, in gluconic acid solution. The calcium sulfate precipitate is removed by filtration, and the solution is refined by barium hydroxide and oxalic acid, and the solution is separated and sedimentated to remove SO42- and Ca2 + in the solution. The gluconic acid solution is then further purified by ion exchange resin. Concentrating the solution to 80-85 percent, adding gluconic acid δ-lactone seeds, concentrating and crystallizing, centrifugally separating, washing and drying.; View all

9. Computational chemical data

Molecular Weight: 178.14000g/mol
Molecular Formula: C₆H₁₀O₆
Compound Is Canonicalized: True
XLogP3-AA: -2
Exact Mass: 178.04773803
Monoisotopic Mass: 178.04773803
Complexity: 181
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 107
Heavy Atom Count: 12
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgOAAAAAAAAAAAAAAAAAAAAAAAAAAkAAAAAAAAAAAAAAAAGgAACAAACBSggAIACAAABgAIAACQCAIAAAAAAAAAAAFAAAABEBYAAAACQAAFIAADAAHKbARAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

How is D-(+)-Glucono-1,5-lactone produced and used in the food industry? Apr 22 2023
D-(+)-Glucono-1,5-lactone is a white crystalline or crystalline powder that is highly soluble in water, slightly soluble in ethanol, and almost insoluble in ether. It slowly hydrolyzes to form gluconi..
What is D-(+)-Glucono-1,5-lactone and how is it used in the food industry? Nov 29 2022
D-(+)-Glucono-1,5-lactone, also known as GDL, is a chelating agent and acidulant used in the food industry. It is commonly referred to as D-GLucono-1,5-lactone or GDL and has the E number E575. It is ..
What should we pay attention to when using D-(+)-Glucono-1,5-lactone? Sep 18 2022
D-(+)-Glucono-1,5-lactone has a wide range of applications, such as in the chemical industry or in some food processing industries. However, the effectiveness and effects may vary in different industr..
What is the role and application of D-(+)-Glucono-1,5-lactone? Jul 29 2022
Every drug has its own purpose and value, and we can feel the help it brings when we use it. However, different drugs have different applications. D-(+)-Glucono-1,5-lactone is not simply a drug, but r..

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