D(+)-Glucose

Iupac Name：(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

CAS No.: 50-99-7

Molecular Weight：180.156

Modify Date.: 2022-11-25 02:16

Introduction: D(+)-glucose ,a short form of dextrorotatory glucose, is a stereoisomer of glucose molecule, which is biologically active and whose bottom chiral carbon has its hydroxyl group (OH) located spatially to the right. Its molecule can exist in an open-chain (acyclic) and ring (cyclic) form and has two isomers α- and β-. It is the main source of energy in the form of ATP for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals, it arises from the breakdown of glycogen in a process known as glycogenolysis. D-(+)-Glucose has been used as a standard for the estimation of total sugar in hydrolyzed starch by phenol-sulfuric acid method. It has also been used in the preparation of the liquid media for culturing some yeast cells. In addition, it is used therapeutically in fluid and nutrient replacement, such as glucose syrup and glucose powder. It can be obtained by enzymatic cleavage of starch, so there are multiple sources like sugar cane, sugar beet, corn (corn syrup), potatoes and wheat. Today, large-scale starch hydrolysis is used to produce glucose. View more+

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1. Names and Identifiers

1.1 Name: D(+)-Glucose
1.2 Synonyms: (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal (3R,4R,5S,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol aldehydo-D-glucose Cerelose 2001 D-(+)-Dextrose D-(+)-Glucose D-(+)-Glucose,Dextrose DEXTROSE,ANHYDROUS,GRANULAR,BIOTECHGRADE DEXTROSE,ANHYDROUS,GRANULAR,REAGENT,ACS DEXTROSE,ANHYDROUS,GRANULAR,USP,EP,BP,JP DEXTROSE,ANHYDROUS,ULTRAPURE D-Glucose-UL-12C6 (depleted of 13C) D-Glucose-UL-13C6, 1,2,3,4,5,6,6-D7 EINECS 207-757-8 MFCD00063684

1.3 CAS No.: 50-99-7

1.4 CID: 107526

1.5 EINECS(EC#): 200-075-1

1.6 Molecular Formula: C6H12O6 (isomer)

1.7 Inchi: InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6+/m0/s1

1.8 InChkey: GZCGUPFRVQAUEE-SLPGGIOYSA-N

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

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

2. Properties

2.1 Density: 1.544

2.1 Melting point: 146℃

2.1 Boiling point: 527.1 °C at 760 mmHg

2.1 Refractive index: 1.573

2.1 Flash Point: 286.7 °C

2.1 Precise Quality: 180.06300

2.1 PSA: 118.22000

2.1 logP: -3.37880

2.1 Solubility: H2O: 1?M at?20?°C, clear, colorless

2.2 Appearance: White crystalline powder

2.3 Storage: Ambient temperatures.

2.4 Autoignition Temperature: Not flammable (USCG, 1999)

2.5 Chemical Properties: White or almost white, crystalline powder.

2.6 Color/Form: White

2.7 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.8 Odor: Odorless

2.9 PH: pH of 0.5 molar aqueous solution = 5.9 /alpha-glucose/

2.10 pKa: pKa 12.43(H2O,t = 18,)(Approximate)

2.11 Water Solubility: H2O: soluble

2.12 Stability: Stable. Substances to be avoided include strong oxidizing agents. Combustible.

2.13 StorageTemp: room temp

3. Use and Manufacturing

3.1 Definition: ChEBI: The open chain form of D-glucose.

3.2 General Description: Watery odorless colorless liquid. Denser than water and soluble in water. Hence sinks in and mixes with water.

3.3 Methods of Manufacturing: 1. Glucose is the most abundant compound present in nature
First, is the product of photosynthesis. It exists in free form in the pulp of plants, especially in fruits, honey, plasma, lymph. Normal human blood glucose content of 0.08% -0.1%, while a greater number of forms of existence is the combination of sugar, starch, glycogen, cellulose and glycosides. Glucose was originally isolated from the grape juice obtained, and hence the name. Industrial production of glucose by hydrolysis of starch obtained in the past with dilute hydrochloric acid hydrolysis of starch, now almost entirely by enzyme hydrolysis instead of dilute hydrochloric acid.
2. Starch hydrolysis available glucose.

3.4 Purification Methods: Crystallise -D-glucose from hot glacial acetic acid or pyridine. Traces of solvent are removed by drying in a vacuum oven at 75o for >3hours. [Gottfried Adv Carbohydr Chem 5 127 1950, Kjaer & Lindberg Acta Chem Scand 1 3 1713 1959, Whistler & Miller Methods in Carbohydrate Chemistry I 1301962, Academic Press, Beilstein 1 IV 4306.] [For equilibrium forms see Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972.] D(+)-Glucose Preparation Products And Raw materials Preparation Products

3.5 Usage: Glucose is the primary fuel for biological respiration. During digestion, complex sugarsand starches are broken down into glucose (as well as fructose and galactose) in the small intestine.Glucose then moves into the bloodstream and is transported to the liver where glucoseis metabolized through a series of biochemical reactions, collectively referred to as glycolysis.Glycolysis, the breakdown of glucose, occurs in most organisms. In glycolysis, the final productis pyruvate. The fate of pyruvate depends on the type of organism and cellular conditions.In animals, pyruvate is oxidized under aerobic conditions producing carbon dioxide. Underanaerobic conditions in animals, lactate is produced. This occurs in the muscle of humansand other animals. During strenuous conditions the accumulation of lactate causes musclefatigue and soreness. Certain microorganisms, such as yeast, under anaerobic conditions convertpyruvate to carbonic dioxide and ethanol. This is the basis of the production of alcohol.Glycolysis also results in the production of various intermediates used in the synthesis of otherbiomolecules. Depending on the organism, glycolysis takes various forms, with numerousproducts and intermediates possible.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S24/25

4.1 RIDADR: NONH for all modes of transport

4.1 Safety Profile: Mildly toxic by ingest ion. An experimental teratogen. Experi mental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Potentially explosive reaction with potassium nitrate + sodium peroxide when heated in a sealed container. Uxtures with alkali release carbon monoxide when heated. When heated to decomposition it emits acrid smoke and irritating fumes.

4.2 WGK Germany: 1

4.2 RTECS: LZ6600000

4.2 Safety: Hazard Codes: Xi,Xn
Risk Statements: 36/37/38-63-62-46-36/38-21
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
R36/38: Irritating to eyes and skin
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36/37-24/25-53-25
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: 1
RTECS: LZ6600000

4.3 Specification: Glucose , its cas register number is 50-99-7. It also can be called Anhydrous dextrose ; Blood sugar ; Cartose ; Cerelose ;
Corn sugar ; D(+)-Glucose ; D-Glucose ; D-Glucose, anhydrous ; Dextropur ; Dextrose ; Dextrose, anhydrous ; Dextrosol ;
Glucolin ; Glucose, anhydrous ; Glucosteril ; Goldsugar ; Grape sugar ; Maxim Energy Gel ; Sirup ; Traubenzucker ; Vadex .

4.4 Toxicity: LD50 orally in Rabbit: 25800 mg/kg

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

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

50-99-7Total: 435 Synthesis Route

50-70-4 553 Suppliers

50-99-7 475 Suppliers

Literatures:
Mizusawa Journal of Biochemistry (Tokyo, Japan),?1933 ,? vol.?18,?p.?253 ????????? ?
Yield: null

57-48-7 281 Suppliers

67-47-0 207 Suppliers

50-99-7 475 Suppliers

Literatures:
RSC Advances, , vol. 3, # 38 p. 17156 - 17165
Yield: ~76%

69-65-8 374 Suppliers

57-48-7 281 Suppliers

50-99-7 475 Suppliers

Literatures:
Chem. Zentralbl., , vol. 90, # III p. 813
Yield: null

View all

8. Precursor and Product

precursor:

50-70-4

50-00-0

69-79-4

69-65-8

57-50-1

57-48-7

product :

526-95-4

80-69-3

97-67-6

60-18-4

89-67-8

547-64-8

67-47-0

50-70-4

73-32-5

488-43-7

527-07-1

79-33-4

108-29-2

110-63-4

488-82-4

116-09-6

56-87-1

492-30-8

499-40-1

620-02-0

57-48-7

140-99-8

473-81-4

87-69-4

97-30-3

View all

9. Other Information

9.0 Description: D-(+)-Glucose is a monosaccharide that occurs in nature and is used by organisms as an energy source. D-(+)-Glucose is the more common enantiomer of L-(–)-glucose (Item No. 20829). Anhydrous Dextrose is the anhydrous form of D-glucose, a natural monosaccharide and carbohydrate. Dextrose serves to replenish lost nutrients and electrolytes. The agent provides metabolic energy and is the primary ingredient in oral rehydration salts (ORS) and is used in intravenous (IV) fluids to provide nutrients to patients under intensive care who are unable to receive them by the oral route. Solutions containing dextrose restore blood glucose levels and provide calories and may aid in minimizing liver glycogen depletion and exerts a protein-sparing action. Dextrose anhydrous also plays a role in the production of proteins and in lipid metabolism. Watery odorless colorless liquid. Denser than water and soluble in water. Hence sinks in and mixes with water. (USCG, 1999) Aldehydo-D-glucose is the open chain form of D-glucose. It is a D-glucose and an aldehydo-glucose. It is an enantiomer of an aldehydo-L-glucose.

9.1 Description: Glucose is one of the most important biological compounds found in nature. It is a main product in photosynthesis and is oxidized in cellular respiration. Glucose polymerizes to form several important classes of biomolecules including cellulose, starch, and glycogen. It also combines with other compounds to produce common sugars such as sucrose and lactose. The form of glucose displayed above is D-glucose. The “D” designation indicates the configuration of the molecule. The “D” configuration specifies that the hydroxyl group on the number 5 carbon is on the right side of the molecule. The mirror image of D-glucose produces another form of glucose called L-glucose.
Glucose is the most common form of a large class of molecules called carbohydrates. Carbohydrates are the predominant type of organic compounds found in organisms and include sugar, starches, and fats. Carbohydrates, as the name implies, derive their name from glucose,C₆H₁₂O₆, which was considered a hydrate of carbon with the general formula of C_n(H₂O)_n, where n is a positive integer. Although the idea of water bonded to carbon to form a hydrate of carbon was wrong, the term carbohydrate persisted. Carbohydrates consist of carbon, hydrogen, and oxygen atoms, with the carbon atoms generally forming long unbranched chains. Carbohydrates are also known as saccharides derived from the Latin word for sugar, saccharon.

9.2 Originator: Dextrose,Wockhardt Ltd.,India

9.3 History: D-Glucose is the most important and predominant monosaccharide found in nature. It was isolated from raisins by Andreas Sigismund Marggraf (1709–1782) in 1747, and in 1838, Jean-Baptiste-André Dumas (1800–1884) adopted the name glucose from the Greek word glycos meaning sweet. Emil Fischer (1852–1919) determined the structure of glucose in the late 19th century. Glucose also goes by the names dextrose (from its ability to rotate polarized light to the right), grape sugar, and blood sugar. The term blood sugar indicates that glucose is the primary sugar dissolved in blood. Glucose’s abundant hydroxyl groups enable extensive hydrogen bonding, and so glucose is highly soluble in water.

9.4 Uses: Glucose is the primary fuel for biological respiration. During digestion, complex sugarsand starches are broken down into glucose (as well as fructose and galactose) in the small intestine.Glucose then moves into the bloodstream and is transported to the liver where glucoseis metabolized through a series of biochemical reactions, collectively referred to as glycolysis.Glycolysis, the breakdown of glucose, occurs in most organisms. In glycolysis, the final productis pyruvate. The fate of pyruvate depends on the type of organism and cellular conditions.In animals, pyruvate is oxidized under aerobic conditions producing carbon dioxide. Underanaerobic conditions in animals, lactate is produced. This occurs in the muscle of humansand other animals. During strenuous conditions the accumulation of lactate causes musclefatigue and soreness. Certain microorganisms, such as yeast, under anaerobic conditions convertpyruvate to carbonic dioxide and ethanol. This is the basis of the production of alcohol.Glycolysis also results in the production of various intermediates used in the synthesis of otherbiomolecules. Depending on the organism, glycolysis takes various forms, with numerousproducts and intermediates possible.

9.5 Uses: D(+)-Glucose anhydrous for biochemistry Reag. Ph Eur. CAS 50-99-7, molar mass 180.16?g/mol.

9.6 Merck: 14,4459

9.7 BRN: 1281608

9.8 References: 1. http://www.sigmaaldrich.com/catalog/product/sigma/g8270?lang=en&region=CA
2. https://pubchem.ncbi.nlm.nih.gov/compound/D-glucose#section=Top
3. http://www.hmdb.ca/metabolites/HMDB00122
4. http://www.biology-online.org/dictionary/D-glucose
5. http://www3.hhu.de/biodidaktik/zucker/sugar/glukose.html

9.9 Chemical Properties: White or almost white, crystalline powder.

9.10 Uses: Dextrose(D-glucose), a simple sugar (monosaccharide), is an important carbohydrate in biology

9.11 Uses: A primary source of energy for living organisms

9.12 Uses: glucose has moisture-binding properties and provides the skin with a soothing effect. It is a sugar that is generally obtained by the hydrolysis of starch.

9.13 Uses: Glucose is a corn sweetener that is commercially made from starch by the action of heat and acids or enzymes, resulting in the complete hydrolysis of the cornstarch. There are two types of refined commercially available: hydrate, which contains 9% by weight water of crystallization and is the most often used, and anhydrous glucose, which contains less than 0.5% water. is a reducing sugar and produces a high-temperature browning effect in baked goods. It is used in ice cream, bakery products, and confections. It is also termed corn sugar.

9.14 Definition: ChEBI: The open chain form of D-glucose.

9.15 Brand name: Cartose (Sterling Winthrop) Dextrose.

9.16 General Description: Watery odorless colorless liquid. Denser than water and soluble in water. Hence sinks in and mixes with water.

9.17 Air & Water Reactions: Water soluble.

9.18 Reactivity Profile: A weak reducing agent.

9.19 Health Hazard: No toxicity

9.20 Safety Profile: Mildly toxic by ingest ion. An experimental teratogen. Experi mental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Potentially explosive reaction with potassium nitrate + sodium peroxide when heated in a sealed container. Uxtures with alkali release carbon monoxide when heated. When heated to decomposition it emits acrid smoke and irritating fumes.

9.21 Purification Methods: Crystallise -D-glucose from hot glacial acetic acid or pyridine. Traces of solvent are removed by drying in a vacuum oven at 75o for >3hours. [Gottfried Adv Carbohydr Chem 5 127 1950, Kjaer & Lindberg Acta Chem Scand 1 3 1713 1959, Whistler & Miller Methods in Carbohydrate Chemistry I 1301962, Academic Press, Beilstein 1 IV 4306.] [For equilibrium forms see Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972.]

9.22 Storage Conditions: 1. Glucose is the most abundant compound present in nature
First, is the product of photosynthesis. It exists in free form in the pulp of plants, especially in fruits, honey, plasma, lymph. Normal human blood glucose content of 0.08% -0.1%, while a greater number of forms of existence is the combination of sugar, starch, glycogen, cellulose and glycosides. Glucose was originally isolated from the grape juice obtained, and hence the name. Industrial production of glucose by hydrolysis of starch obtained in the past with dilute hydrochloric acid hydrolysis of starch, now almost entirely by enzyme hydrolysis instead of dilute hydrochloric acid.
2. Starch hydrolysis available glucose.

9.23 Storage features: Separated from strong oxidants. Well closed.

9.24 Usage: D-Glucose is used in various metabolic processes including enzymic synthesis of cyclohexyl-alpha and beta -D-glucosides. It is involved in the detection of type 2 diabetes mellitus and the most widely used aldohexose in living organisms. Its availability influences psychological processes since it is a primary energy source for the brain.

9.25 Usage: D-(+)-Glucose used as a ideal in culture media component. Also used in foods and medicines and as a source of certain amino acids by fermentation.

10. Computational chemical data

Molecular Weight: 180.156g/mol
Molecular Formula: C₆H₁₂O₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 180.06338810
Monoisotopic Mass: 180.06338810
Complexity: 138
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 118
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: AAADccBgOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACBSggAIAAAAAAgAIAAgQgAIAAAAAAAAAAAFAAAABEBYAAAAAQAAFIAABAAHKbARAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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Chemical product D(+)-Glucose