L-Arabinose
Synonym(s):L(+)-Arabinose;Pectin sugar;Pectinose
- CAS NO.:87-72-9
- Empirical Formula: C5H10O5
- Molecular Weight: 150.13
- MDL number: MFCD00006609
- EINECS: 201-767-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-28 23:16:16
What is L-Arabinose?
Chemical properties
White to off white crystalline powder
The Uses of L-Arabinose
A base component of hemicellulose and pectin, critical biopolymers.
The Uses of L-Arabinose
L-(+)-Arabinose is used to identify and differentiate and characterize pentose sugar isomerase. It is also used as the carbon source in microbial culture. It is involved in the bioproduction of L-ribose. It finds application in the production of savory reaction flavors. Its derivatives are used in the development of antiviral agents such as nucleoside. It acts as a base component of hemicellulose and pectin.
Definition
ChEBI: L-arabinopyranose is the six-membered ring form of L-arabinose. It has a role as an Escherichia coli metabolite and a mouse metabolite.
Purification Methods
beta-L-(+)-Arabinose is recrystallised slowly, twice, from 80% aqueous EtOH, then dried under vacuum over P2O5. It can also be purified by heating the arabinose (200g) with glacial acetic acid (300mL) on a boiling water bath for 45minutes, cooling, filtering, washing with 95% EtOH (500mL) in four portions and drying at 56-60o over P2O5. It has been recrystallised from 5times its weight of 76% EtOH using charcoal (10g) to yield 127g, m 155-157o, [] 20D +190.6o and mutarotating to +104o (c 4, H2O). [Anderson & Sands Org Synth Coll Vol I 67 1941, Wolfrom & Christian J Am Chem Soc 48 3172 1926, Beilstein 1 IV 4217.]
Mode of action
L-arabinose has been shown to slow down glucose absorption by inhibiting the intestinal enzyme sucrase in an uncompetitive manner. Sucrase is present in the brush border of the intestine and critical for hydrolysing sucrose into a glucose and fructose molecule[1].
Mode of action
[1] Korrie Pol, Monica Mars, Marie-Luise Puhlmann. “Efficacy of L-Arabinose in Lowering Glycemic and Insulinemic Responses: The Modifying Effect of Starch and Fat.” Foods (2022).
Properties of L-Arabinose
Melting point: | 160-163 °C(lit.) |
Boiling point: | 191.65°C (rough estimate) |
alpha | 103 º (c=5, H2O) |
Density | 1.1897 (rough estimate) |
refractive index | 1.3920 (estimate) |
storage temp. | Inert atmosphere,Room Temperature |
solubility | Methanol (Slightly), Water (Sparingly) |
pka | 12.26±0.70(Predicted) |
form | Fine Crystalline Powder |
color | White |
Water Solubility | soluble |
Merck | 14,761 |
BRN | 1723085 |
CAS DataBase Reference | 87-72-9(CAS DataBase Reference) |
NIST Chemistry Reference | Arabinose(L)(87-72-9) |
EPA Substance Registry System | L-Arabinopyranose (87-72-9) |
Safety information for L-Arabinose
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for L-Arabinose
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