A6390

β-D-Allose

Name: β-<SC>D</SC>-Allose
Brand: SIGMA

rare aldohexose sugar

Synonym(s):

β-D-Allopyranose

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About This Item

Empirical Formula (Hill Notation):

C₆H₁₂O₆

CAS Number:

7283-09-2

Molecular Weight:

180.16

NACRES:

NA.25

PubChem Substance ID:

24891083

UNSPSC Code:

12352201

MDL number:

MFCD00063268

Key Documents

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Product Name

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

Related Categories

Biochemicals

Carbohydrates for Biochemical Research

Cell Culture Supplements & Reagents

Chemical Biology

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This Item	I7253	A7791	G0259
Sigma-Aldrich A6390 β-D-Allose	Sigma-Aldrich I7253 Isomaltose	Sigma-Aldrich A7791 N-Acetyl-D-lactosamine	Sigma-Aldrich G0259 D-Glucosaminic acid
technique(s) HPLC: suitable, thin layer chromatography (TLC): suitable	technique(s) thin layer chromatography (TLC): suitable	technique(s) thin layer chromatography (TLC): suitable	technique(s) thin layer chromatography (TLC): suitable
assay ≥98% (HPLC), ≥98% (TLC)	assay ~98% (TLC)	assay ≥98% (TLC)	assay ≥98% (TLC)
solubility water: 49.00-51.00 mg/mL, clear, colorless to light yellow	solubility water: 49.00-51.00 mg/mL, clear, colorless to faintly yellow	solubility water: 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow	solubility 0.5 M HCl: 50 mg/mL, clear, colorless to faintly yellow
Quality Level 200	Quality Level 200	Quality Level 100	Quality Level 100
form powder	form lyophilized powder	form powder	form powder
impurities <2.00% water (Karl Fischer)	impurities -	impurities ≤8% water	impurities -

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.[1] D-Allose upregulates thioredoxin-interacting protein (TXNIP) gene expression and was found to induce G1 cell cycle arrest in hepatocellular carcinoma cells.[2] It inhibited transcriptional activity of the activator protein 1, nuclear factor-κB, and nuclear factor of activated T cells.[3] D-Allose decreases transport of 2-deoxy-D-glucose and 3-O-methyl-D-glucose in V79 Chinese hamster lung fibroblast cells.[4]

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.

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number

0000458312

0000431669

0000403546

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Characterization of the D-allose-mediated regulation of sugar transport in Chinese hamster fibroblasts.

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

Rare sugar D-allose induces specific up-regulation of TXNIP and subsequent G1 cell cycle arrest in hepatocellular carcinoma cells by stabilization of p27kip1.

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

Rare sugar D-allose strongly induces thioredoxin-interacting protein and inhibits osteoclast differentiation in Raw264 cells.

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).

Activated mTORC1 promotes long-term cone survival in retinitis pigmentosa mice.

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

Microbial metabolism and biotechnological production of D-allose.

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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