D-Ribose Chemical Properties

Melting point:

88-92 °C(lit.)

alpha 

-20.8 º (c=4, H2O)

Boiling point:

191.65°C (rough estimate)

Density 

1.1897 (rough estimate)

refractive index 

-21 ° (C=1, H2O)

FEMA 

3793 | D-RIBOSE

storage temp. 

2-8°C

solubility 

H₂O: 0.1 g/mL, clear, colorless to light yellow

pka

12.46±0.20(Predicted)

form 

Crystalline Powder

color 

White to light beige or slightly yellow

PH Range

7

optical activity

[α]21/D 19.7°, c = 4 in H2O

Water Solubility 

Soluble in water. Insoluble in ether.

Sensitive 

Hygroscopic

Merck 

14,8204

BRN 

1723081

InChIKey

HMFHBZSHGGEWLO-SOOFDHNKSA-N

LogP

-1.47

CAS DataBase Reference

50-69-1(CAS DataBase Reference)

NIST Chemistry Reference

D-Ribose(50-69-1)

EPA Substance Registry System

D-Ribose (50-69-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

24/25-37/39-26

WGK Germany 

3

RTECS 

VJ2275000

F 

3-10

TSCA 

Yes

HS Code 

29400090

MSDS

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D-Ribose Usage And Synthesis

Description

D-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 Properties

D-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.

Occurrence

Reported found in boiled crab, hen egg, catfish, whitefish, haddock, stored beef, stored veal, milk, applesauce, potato, rapeseed, roasted coffee, fresh coffee and shrimp.

Uses

D-Ribose is produced by microorganism fermentation of glucose in a fermentation culture medium without adding calcium carbonate.

Preparation

D-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)

Definition

ChEBI: 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 Functions

D-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 Activity

D-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 Actions

Ribose is an aldopentose monosaccharide that is phosphorylated into D-ribose 5-phosphate by ribokinase.

Side effects

D-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 Methods

Crystallise -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.

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