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Merck

A6390

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
NACRES:
NA.25
PubChem Substance ID:
24891083
UNSPSC Code:
12352201
MDL number:
MFCD00063268

Nom du produit

β-D-Allose, rare aldohexose sugar

InChI key

WQZGKKKJIJFFOK-QZABAPFNSA-N

SMILES string

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

assay

≥98% (HPLC)
≥98% (TLC)

form

powder

optical activity

[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

impurities

<2.00% water (Karl Fischer)

color

white to yellow cast

solubility

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

Quality Level

200

Catégories apparentées

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.

Biochem/physiol Actions

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.

Other Notes

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

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
0000458312
0000458312
0000431669
0000431669
0000403546

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Consulter la Bibliothèque de documents

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).
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
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
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