Erythrose

Erythrose[1]

D-Erythrose

L-Erythrose
Names
IUPAC names
(2R,3R)-2,3,4-Trihydroxybutanal (D)
(2S,3S)-2,3,4-Trihydroxybutanal (L)
Identifiers
583-50-6 (D) YesY
533-49-3 (L) YesY
ChEBI CHEBI:27904 YesY
ChemSpider 84990 (D) YesY
Jmol interactive 3D (D): Image
(L): Image
PubChem 94176 (D)
Properties
C4H8O4
Molar mass 120.10 g·mol−1
Appearance Light yellow syrup
Very soluble
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Erythrose is a tetrose carbohydrate with the chemical formula C4H8O4. It has one aldehyde group, and so is part of the aldose family. The natural isomer is D-erythrose.

Fischer projections

Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869),[2] and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").[3][4]

Erythrose' is an anti-cancer agent. In vitro, ~4mM erythrose effectively kills cancer cells for tested cell lines in vitro, such as: lung, brain,breast,and colorectal cancers, etc. [5]

D-Erythrose inhibits tumor growth in vivo. [6]

Erythrose is a 2/3 of Glucose. Diabetes can have blood sugar (mainly glucose)up to 30mM for days. The concentration of erythrose to kill cancer is much lower than glucose in our body. What Erythrose can do for cancer patients needs further study.

Erythrose, as glucose, can be oxidized to carbon dioxide and water.[7]

Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway[8] and the Calvin cycle.[9]

Oxidative bacteria can be made to use erythrose as its sole energy source.[10]

References

  1. Merck Index, 11th Edition, 3637
  2. Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
  3. Garot (1850) "De la matière colorante rouge des rhubarbes exotiques et indigènes et de son application (comme matière colorante) aux arts et à la pharmacie" (On the red coloring material of exotic and indigenous rhubarb and on its application (as a coloring material) in the arts and in pharmacy), Journal de Pharmacie et de Chimie, 3rd series, 17 : 5-19. Erythrose is named on p. 10: "Celui que je propose, sans y attacher toutefois la moindre importance, est celui d'érythrose, du verbe grec 'ερυθραινω, rougir (1)." (The one [i.e., name] that I propose, without attaching any importance to it, is that of erythrose, from the Greek verb ερυθραινω, to redden (1).)
  4. Wells, David Ames; Cross, Charles Robert; Bliss, George; Trowbridge, John; Nichols, William Ripley; Kneeland, Samuel (1851). Annual of Scientific Discovery. Boston: Gould, Kendall, and Lincoln. p. 211. Retrieved 11 December 2014.
  5. Wang X and Wei Y 2010 “Erythrose kill cancer cell in vitro and inhibit tumor growth in vivo” American Association for Cancer Research 101st Conference.
  6. LILI LIU, TAO YI and XIA ZHAO 2015. Antitumor effect of D-erythrose in an abdominal metastatic model of colon carcinoma ONCOLOGY LETTERS 9: 769-773, 2015
  7. Batt RD, Dickens F, Williamson DH. 1960. Tetrose metabolism 2. The utilization of tetroses and tetritols by rat tissues. Biochem J. 77:281-94.
  8. Kruger, Nicholas J; von Schaewen, Antje (June 2003). "The oxidative pentose phosphate pathway: structure and organisation". Current Opinion in Plant Biology 6 (3): 236–246. doi:10.1016/S1369-5266(03)00039-6. Retrieved 11 December 2014.
  9. Schwender, Jörg; Goffman, Fernando; Ohlrogge, John B.; Shachar-Hill, Yair (9 December 2004). "Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds". Nature 432 (7018): 779–782. doi:10.1038/nature03145. Retrieved 11 December 2014.
  10. Hiatt, Howard H; Horecker, B L (13 October 1955). "D-erythrose metabolism in a strain of Alcaligenes faecalis". Journal of Bacteriology 71 (6): 649–654. Retrieved 11 December 2014.
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