A6390

Sigma-Aldrich

β-D-Allose

rare aldohexose sugar

Synonym(s):
β-D-Allopyranose
Empirical Formula (Hill Notation):
C6H12O6
CAS Number:
Molecular Weight:
180.16
MDL number:
PubChem Substance ID:

Quality Level

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

application(s)

HPLC: suitable
thin layer chromatography (TLC): suitable

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

InChI key

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.

Packaging

1 g in glass bottle
250 mg in glass bottle

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.

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
Nicholas J Bradshaw et al.
PloS one, 9(10), e111196-e111196 (2014-10-22)
We have previously proposed that specific proteins may form insoluble aggregates as a response to an illness-specific proteostatic dysbalance in a subset of brains from individuals with mental illness, as is the case for other chronic brain conditions. So far...

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service