D-Ribose CAS 50-69-1

Introduction:Basic information about D-Ribose CAS 50-69-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

D-Ribose Basic information

Product Name:D-Ribose
Synonyms:RIBOSE, D-(-)-;d-ribos;D-RIB;D(-)-Ribose,99+%;R-RIBOSE;RIBONIC ACID-Gamma-LACTONE, D-(+)-(RG);Ribose (300 mg);D-Ribose/D(-)-Ribose
CAS:50-69-1
MF:C5H10O5
MW:150.13
EINECS:200-059-4
Product Categories:Sugars, Carbohydrates & Glucosides;FINE Chemical & INTERMEDIATES;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Nucleosides, Nucleotides & Related Reagents;Ribose;Riboses and 2'-Deoxyriboses;Sugars;Nutritional Supplements;Nutritional fortification substances;Carbohydrates & Derivatives;Co-factor/nucleoside;Alphabetical Listings;Flavors and Fragrances;Q-Z;Biochemicals Found in Plants;MonosaccharidesBiochemicals Found in Plants;Simple sugars;Carbohydrate Synthesis;Carbohydrates;Specialty Synthesis;Carbohydrate LibraryBiochemicals Found in Plants;CarbohydrateMetabolomics;Metabolic Libraries;Metabolic Pathways;Metabolites and Cofactors on the Metabolic Pathways Chart;50-69-1;Glycon Biochem
Mol File:50-69-1.mol

D-Ribose Chemical Properties

Melting point 88-92 °C(lit.)
alpha -20.8 º (c=4, H2O)
Boiling point 191.65°C (rough estimate)
bulk density480kg/m3
density 1.1897 (rough estimate)
FEMA 3793 | D-RIBOSE
refractive index -21 ° (C=1, H2O)
storage temp. 2-8°C
solubility H2O: 0.1 g/mL, clear, colorless to light yellow
pKa12.46±0.20(Predicted)
form Crystalline Powder
color White to light beige or slightly yellow
PH7 (20°C, 10g/L in H2O)
PH Range7
Optical Rotation[α]21/D 19.7°, c = 4 in H2O
biological sourcemicrobial (fermentation)
Water Solubility Soluble in water. Insoluble in ether.
Sensitive Hygroscopic
Merck 14,8204
BRN 1723081
Major Applicationflavors and fragrances
Cosmetics Ingredients FunctionsSKIN CONDITIONING
HUMECTANT
InChI1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m0/s1
InChIKeyHMFHBZSHGGEWLO-SOOFDHNKSA-N
SMILESOC[C@@H](O)[C@@H](O)[C@@H](O)C([H])=O
LogP-1.47
CAS DataBase Reference50-69-1(CAS DataBase Reference)
NIST Chemistry ReferenceD-Ribose(50-69-1)
EPA Substance Registry SystemD-Ribose (50-69-1)
CAS Number Unlabeled50-69-1

Safety Information

Hazard Codes Xi
Risk Statements 36/38
Safety Statements 24/25-37/39-26
WGK Germany 3
RTECS VJ2275000
3-10
TSCA TSCA listed
HS Code 29400090
Storage Class11 - Combustible Solids

D-Ribose Usage And Synthesis

DescriptionD-ribose is an important five-carbon monosaccharide with the chemical formula C5H10O5. It is an important constituent of ribonucleic acid (RNA) and ATP, and plays an important role in the formation of life. It is also an important pharmaceutical intermediate for the production of various nucleic acid drugs.
Chemical PropertiesD-Ribose is a five-carbon sugar with strong water solubility and sweet taste, also known as D-ribofuranose. It is used by all living cells and is an essential component in living organisms for energy production. It is widely present in the furan form.
OccurrenceReported found in boiled crab, hen egg, catfish, whitefish, haddock, stored beef, stored veal, milk, applesauce, potato, rapeseed, roasted coffee, fresh coffee and shrimp.
UsesD-Ribose is produced by microorganism fermentation of glucose in a fermentation culture medium without adding calcium carbonate.
PreparationD-Ribose is obtained by using D-glucose as a raw material, inserting bacteria or Bacillus subtilis for fermentation, and separating and refining the fermentation product.(By fermentation technology)
DefinitionChEBI: D-ribose is a ribofuranose having D-configuration. It is a naturally occurring monosaccharide found in the cells and particularly in the mitochondria is essential in energy production.
Biological FunctionsD-ribose is a penta-sugar precursor of some amino acids like glutamate, histidine, proline, and arginine. This substance is transformed into piruvate, enters Krebs's cycle, and has a crucial role in energetic metabolism; it is also involved in glycogen synthesis. The non-oxidative transketolase PPP reaction can be directly synthesized by transferring a keto group to glyceraldehyde 3-phoshate from fructose 6-phosphate. Both these substrates are intermediate products of glycolysis[1].
Biological ActivityD-ribose is a natural sugar that our bodies produce for a variety of purposes most notably encrgy in the form of ATP(adenosine triphosphate), which powers every cell in our body. Ribose is crucial for the synthesis of energy (ATP) and without it, your cells run out of energy and the health of the cell is compromised. Supplementing with ribose improves cell function by restoring energy.
One of the most vital organs to suffer energy depletion is the heart. That is why so much of the research on D-ribose has focused on the impact of supplement ribose in heart disease. Although ribose is classified as a sugar, when taken orally, it does not have any impact on blood sugar like glucose. Instead, it is used for energy production and energy recovery. Every cell in the body has the capacity to make ribose. But more ribose may be needed than the cell can produce when cells are metabolically stressed, such as with strenuous exercise or disease. When the cells are metabolically stressed they tend to consume more glucose rather than producing more ribose. This can dramatically affect recovery.
Biochem/physiol ActionsRibose is an aldopentose monosaccharide that is phosphorylated into D-ribose 5-phosphate by ribokinase.
Side effectsD-ribose is a dietary supplement approved by the US FDA. It is generally considered safe for dosage of ribose is less than 15g/d. However, possible side effects include diarrhea, stomach discomfort, nausea, headache, and low blood sugar.
Purification MethodsCrystallise -D(-)-ribose from aqueous 80% EtOH, dry it under vacuum at 60o over P2O5 and store it in a vacuum desiccator. It exhibits a complex mutarotation with : [] D 10 -23.1o (1.5minutes), -21.3o (5minutes), -19.5o (10minutes), -19.1o (30minutes), -21.2o (60minutes), -23.1o (120minutes), -23.7o (300minutes), (c 4.5, H2O) [Phelps et al. J Am Chem Soc 56 748 1934]. 1H NMR in D2O at 44o shows 17% -pyranose, 59% -pyranose, 9% -furanose and 15% -furanose forms with furanose -H at 5.34ppm (J 3.0Hz) and -H at 5.31 (J 1.7Hz) [Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972]. The phenylhydrazone crystallises from aqueous pyridine in yellow needles, m 163-164o, and the benzylphenylhydrazone has m 127-128o [Snowden J Am Chem Soc 72 808 1950.] [Beilstein 1 IV 4211.]
References[1] Simonetta Croci. “Potassium bicarbonate and D-ribose effects on A72 canine and HTB-126 human cancer cell line proliferation in vitro.” Cancer Cell International 11 (2011): 30.

D-Ribose Preparation Products And Raw materials

Raw materialsD(+)-Glucose-->3-amino-3,6-didesoxyglucose-->D-Glyceraldehyde-->Water-->GLYCOLALDEHYDE-->D-Galactose
Preparation ProductsSPINOSAD-->Spinosad D-->Ribavirin-->Coenzyme A-->5-Deoxy-D-ribose-->D-(-)-THREOSE-->2,3,5-TRI-O-BENZYL-L-ARABINOFURANOSE-->5'-Guanylic acid-->2-O,3-O,4-O,5-O-Tetrakis(trimethylsilyl)-D-ribose-->D-RIBOSE-5-PHOSPHATE DISODIUM SALT
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