Ribitol

Names

[ CAS No. ]:
488-81-3

[ Name ]:
Ribitol

[Synonym ]:
(2R,3s,4S)-1,2,3,4,5-Pentanpentol
adonitol
ADONIT
ADONITE
ADONITOL(RG)
(2R,3s,4S)-pentane-1,2,3,4,5-pentol
RIBITO
Adonito
D-erythro-Pentitol
MFCD00064291
D-Ribitol
meso ribitol
Ribitol
(2R,3s,4S)-1,2,3,4,5-Pentanepentol
Adonite Ribitol
EINECS 207-685-7
Adonite,Ribitol
meso-ribitol
D-(+)-Arabitol
Adonitrol

Biological Activity

[Description]:

Ribitol is a crystalline pentose alcohol formed by the reduction of ribose. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol.

[Related Catalog]:

Research Areas >> Others

Natural Products >> Saccharides and Glycosides

[Target]

Human Endogenous Metabolite

[In Vitro]

Ribitol is a reduced sugar[1]. Phosphoglucose isomerase-deficient (pgi1) strains of Saccharomyces cerevisiae are studied for the production of D-ribose and Ribitol from D-glucose via the intermediates of the pentose phosphate pathway. Overexpression of the gene encoding sugar phosphate phosphatase (DOG1) of S. cerevisiae is needed for the production of D-ribose and Ribitol. The engineered strains are compared for their ability to produce the PPP-derived 5-carbon compounds Ribitol and D-ribose from D-glucose[2].

[Kinase Assay]

The high-performance liquid chromatography (HPLC) analyses are carried out using a Fast Acid Column (100×7.8 mm) and a HPX-87H Ion Exclusion Column (300 mm×7.8 mm) in series with 2.5 mM H2SO4 in water as the mobile phase at a flow rate of 0.3 mL/min, at 55°C. This method enabled quantification of D-glucose, ethanol, glycerol, D-xylulose, Ribitol, and xylitol. D-ribose, D-ribulose, and D-arabitol coeluted on the Aminex HPX-87H column. The CarboPac MA-1 column of Dionex ICS-3000 is used to analyze representative culture supernatant samples for the presence of arabitol and xylitol. Samples are run at column temperature of 30°C with 480 mM NaOH at flow rate 0.4 mL/min. The CarboPac MA-1 column separated D-arabitol from D-ribose and D-ribulose, but the alkaline conditions degraded D-ribulose interfering with the quantification of D-ribose.Yeast cells are disrupted with glass beads in 100 mM sodium phosphate buffer pH 7.0 containing phenylmethylsulfonyl fluoride and pepstatin A in final concentrations of 0.17 mg/mL and 0.01 mg/mL, respectively.The activity of NAD+-dependent Gdh2p is measured in a reaction buffer of 0.5 M triethanol amine pH 7.7 and 2 mM NADH. After addition of the cell lysate, the reaction is started by adding a mixture of α-ketoglutarate (100 mM) and NH4Cl (200 mM) to a final concentration of 2.4 mM and 4.9 mM, respectively. The GapB activity is measured. Shortly, the reaction mixture is 500 mM triethanol amine pH 7.8, 1 mM ATP, 2 mM MgCl2, 200 μM NADPH, and 10 μg/mL of phosphoglycerate kinase. 3-phosphoglycerate is added to a final concentration of 5 mM to start the reaction. Activity measurements are performed with a Cobas Mira Plus automated analyzer[2].

[References]

[1]. Praissman JL, et al. The functional O-mannose glycan on α-dystroglycan contains a phospho-Ribitol primed for matriglycan addition. Elife. 2016 Apr 29;5. pii: e14473.

[2]. Toivari MH, et al. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol. Appl Microbiol Biotechnol. 2010 Jan;85(3):731-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
494.5±40.0 °C at 760 mmHg

[ Melting Point ]:
101-104ºC

[ Molecular Formula ]:
C₅H₁₂O₅

[ Molecular Weight ]:
152.146

[ Flash Point ]:
261.9±21.9 °C

[ Exact Mass ]:
152.068466

[ PSA ]:
101.15000

[ LogP ]:
-3.77

[ Vapour Pressure ]:
0.0±2.9 mmHg at 25°C

[ Index of Refraction ]:
1.571

[ Storage condition ]:
Store at RT.

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VJ0800000

CHEMICAL NAME :: Ribitol

CAS REGISTRY NUMBER :: 488-81-3

BEILSTEIN REFERENCE NO. :: 1720524

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C5-H12-O5

MOLECULAR WEIGHT :: 152.17

WISWESSER LINE NOTATION :: Q1YQYQYQ1Q -RIB

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 35,98,1936 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X9704 No. of Facilities: 116 (estimated) No. of Industries: 2 No. of Occupations: 6 No. of Employees: 2181 (estimated) No. of Female Employees: 1615 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
VJ0800000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Urinary metabolic fingerprinting of mice with diet-induced metabolic derangements by parallel dual secondary column-dual detection two-dimensional comprehensive gas chromatography.

J. Chromatogr. A. 1361 , 265-76, (2014)

This study investigates the potential of a parallel dual secondary column-dual detection two-dimensional comprehensive GC platform (GC×2GC-MS/FID) for metabolic profiling and fingerprinting of mouse u...

Proteomic and metabolomic analysis of the carotenogenic yeast Xanthophyllomyces dendrorhous using different carbon sources.

BMC Genomics 16 , 289, (2015)

Astaxanthin is a potent antioxidant with increasing biotechnological interest. In Xanthophyllomyces dendrorhous, a natural source of this pigment, carotenogenesis is a complex process regulated throug...

Selective removal of phosphate for analysis of organic acids in complex samples.

J. Chromatogr. A. 1388 , 1-8, (2015)

Accurate quantitation of compounds in samples of biological origin is often hampered by matrix interferences one of which occurs in GC-MS analysis from the presence of highly abundant phosphate. Conse...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.