Sedoheptulose

Sedoheptulose
Names
IUPAC name
D-altro-Hept-2-ulose[1]
Systematic IUPAC name
(3S,4R,5R,6R)-1,3,4,5,6,7-Hexahydroxyheptan-2-one
Other names
D-altro-2-Heptulose; D-altro-Heptulose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.019.243 Edit this at Wikidata
MeSH Sedoheptulose
UNII
  • InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5-,6-,7-/m1/s1 checkY
    Key: HSNZZMHEPUFJNZ-SHUUEZRQSA-N checkY
  • InChI=1/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5-,6-,7-/m1/s1
    Key: HSNZZMHEPUFJNZ-SHUUEZRQBR
  • O=C([C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO)CO
Properties
C7H14O7
Molar mass 210.182 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Sedoheptulose or pseudoheptulose or D-altro-heptulose is a ketoheptose—a monosaccharide with seven carbon atoms and a ketone functional group. It is one of the few heptoses found in nature, and is found in various fruits and vegetables ranging from carrots and leeks to figs, mangos and avocados.[2][3]

It is an intermediate in respiratory and photosynthetic pathways and plays a vital role in the non-oxidative branch of the pentose phosphate pathway.[4][5]

Studies have shown that 7-O-galloyl-D-sedoheptulose, a chemical extracted from dogwood fruit, is able to reduce pro-inflammatory markers in vivo such as interleukin-6 (IL-6) and C-reactive protein and thus might be able reduce low-level inflammation in humans.[6] While this compound contains a sedoheptulose moiety, sedoheptulose itself has not been shown to possess the same properties.

  1. ^ "2-Carb-10". iupac.qmul.ac.uk. Retrieved 2023-11-14.
  2. ^ Ogata, James N.; Kawano, Yoshihiko; Bevenue, Arthur; Casarett, Louis J. (January 1972). "Ketoheptose content of some tropical fruits". Journal of Agricultural and Food Chemistry. 20 (1): 113–115. doi:10.1021/jf60179a011. PMID 5059931.
  3. ^ Okuda, Takuo; Mori, Kazuko (June 1974). "Distribution of manno-heptulose and sedoheptulose in plants". Phytochemistry. 13 (6): 961–964. Bibcode:1974PChem..13..961O. doi:10.1016/S0031-9422(00)91430-4.
  4. ^ Horecker, B. L; Smyrniotis, P. Z (1953). "Transaldolase: The Formation of Fructose-6-Phosphate from Sedoheptulose-7-Phosphate". Journal of the American Chemical Society. 75 (8): 2021. doi:10.1021/ja01104a532.
  5. ^ Patra, Krushna C; Hay, Nissim (2014). "The pentose phosphate pathway and cancer". Trends in Biochemical Sciences. 39 (8): 347–354. doi:10.1016/j.tibs.2014.06.005. PMC 4329227. PMID 25037503.
  6. ^ Park, Chan Hum; Tanaka, Takashi; Yokozawa, Takako (September 2013). "Evaluation of 7-O-galloyl-d-sedoheptulose, isolated from Corni Fructus, in the adipose tissue of type 2 diabetic db/db mice". Fitoterapia. 89: 131–142. doi:10.1016/j.fitote.2013.03.026. ISSN 0367-326X. PMID 23567861.