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A6390

Sigma-Aldrich

β-D-Allose

rare aldohexose sugar

Synonyme(s) :

β-D-Allopyranose

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About This Item

Formule empirique (notation de Hill):
C6H12O6
Numéro CAS:
7283-09-2
Poids moléculaire :
180.16
Numéro MDL:
MFCD00063268
Code UNSPSC :
12352201
ID de substance PubChem :
24891083
Nomenclature NACRES :
NA.25

Niveau de qualité

200

Pureté

≥98% (HPLC)
≥98% (TLC)

Forme

powder

Activité optique

[α]/D 12.00 to 16.00 °, c = 45.00-55.00 mg/mL in water

Technique(s)

HPLC: suitable
thin layer chromatography (TLC): suitable

Impuretés

<2.00% water (Karl Fischer)

Couleur

white to yellow cast

Solubilité

water: 49.00-51.00 mg/mL, clear, colorless to light yellow

Chaîne SMILES 

OC[C@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O

InChI

1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6-/m1/s1

Clé InChI

WQZGKKKJIJFFOK-QZABAPFNSA-N

Application

β-D-Allose (β-D-Allose), a rare sugar member of the aldohexose family and a C3 epimer of glucose, is used as an inhibitor of fruiting body formation and sporulation in Myxococcus xanthus.

Actions biochimiques/physiologiques

D-Allose is a rare aldohexose sugar that has demonstrated anti-cancer, antitumor, anti-inflammatory, anti-oxidative, antihypertensive, cryoprotective, and immunosuppressant activities. D-Allose upregulates thioredoxin-interacting protein (TXNIP) gene expression and was found to induce G1 cell cycle arrest in hepatocellular carcinoma cells. It inhibited transcriptional activity of the activator protein 1, nuclear factor-κB, and nuclear factor of activated T cells. D-Allose decreases transport of 2-deoxy-D-glucose and 3-O-methyl-D-glucose in V79 Chinese hamster lung fibroblast cells.

Autres remarques

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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R J Germinario et al.
Journal of cellular physiology, 145(2), 318-323 (1990-11-01)
Exposure to D-allose has been demonstrated to lead to decreased 2-deoxy-D-glucose (2-DG) and 3-0-methyl-D-glucose transport in the V79 Chinese hamster lung fibroblast cell line. The effect of D-allose 1) was maximal after 4 hours exposure to the cells; 2) was
Fuminori Yamaguchi et al.
International journal of oncology, 32(2), 377-385 (2008-01-19)
'Rare sugars' are defined as monosaccharides that exist in nature but are only present in limited quantities. The development of mass production method of rare sugars revealed some interesting physiological effects of these on animal cells, but the mechanisms have
Kana Yamada et al.
Nutrition research (New York, N.Y.), 32(2), 116-123 (2012-02-22)
Oxidative stress modulates the osteoclast differentiation via redox systems, and thioredoxin 1 (Trx) promotes the osteoclast formation by regulating the activity of transcription factors. The function of Trx is known to be regulated by its binding partner, thioredoxin-interacting protein (TXNIP).
Aditya Venkatesh et al.
The Journal of clinical investigation, 125(4), 1446-1458 (2015-03-24)
Retinitis pigmentosa (RP) is an inherited photoreceptor degenerative disorder that results in blindness. The disease is often caused by mutations in genes that are specific to rod photoreceptors; however, blindness results from the secondary loss of cones by a still
Yu-Ri Lim et al.
Applied microbiology and biotechnology, 91(2), 229-235 (2011-06-10)
D-allose has attracted a great deal of attention in recent years due to its many pharmaceutical activities, which include anti-cancer, anti-tumor, anti-inflammatory, anti-oxidative, anti-hypertensive, cryoprotective, and immunosuppressant activities. D-allose has been produced from D-psicose using D-allose-producing enzymes, including L-rhamnose isomerase
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