Sedoheptulose

Sedoheptulose
Names
	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
CAS Number	3019-74-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16802 ;
ChemSpider	4573620 ;
ECHA InfoCard	100.019.243
MeSH	Sedoheptulose
PubChem CID	5459879;
UNII	40A0W1XJ6X ;
CompTox Dashboard (EPA)	DTXSID10952581 ;
	InChI 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 Key: HSNZZMHEPUFJNZ-SHUUEZRQSA-N ; 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;
	SMILES O=C([C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO)CO;
Properties
Chemical formula	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).
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	Infobox references

Sedoheptulose 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.[1][2]

It is an intermediate in respiratory and photosynthetic pathways and plays a vital role in the non-oxidative branch of the pentose phosphate pathway.[3][4]

Studies have shown that sedoheptulose is able to reduce pro-inflammatory markers in vitro such as interleukin-6 (IL-6) and C-reactive protein and thus might be able reduce low-level inflammation in humans.[5]

Furthermore, the absence of dietary sedoheptulose and related heptoses can trigger the development of cystinosis when coupled with a rare genetic defect.[6]

References

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.
Okuda, Takuo; Mori, Kazuko (June 1974). "Distribution of manno-heptulose and sedoheptulose in plants". Phytochemistry. 13 (6): 961–964. doi:10.1016/S0031-9422(00)91430-4.
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.
Patra, Krushna C; Hay, Nissim (2014). "The pentose phosphate pathway and cancer". Trends in Biochemical Sciences. 39 (8): 347. doi:10.1016/j.tibs.2014.06.005. PMC 4329227. PMID 25037503.
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.
Kardon, Tamas; Stroobant, Vincent; Veiga-da-Cunha, Maria; Schaftingen, Emile Van (15 October 2008). "Characterization of mammalian sedoheptulokinase and mechanism of formation of erythritol in sedoheptulokinase deficiency". FEBS Letters. 582 (23–24): 3330–3334. doi:10.1016/j.febslet.2008.08.024. PMID 18775706.

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[1] 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.

[2] Okuda, Takuo; Mori, Kazuko (June 1974). "Distribution of manno-heptulose and sedoheptulose in plants". Phytochemistry. 13 (6): 961–964. doi:10.1016/S0031-9422(00)91430-4.

[3] 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.

[4] Patra, Krushna C; Hay, Nissim (2014). "The pentose phosphate pathway and cancer". Trends in Biochemical Sciences. 39 (8): 347. doi:10.1016/j.tibs.2014.06.005. PMC 4329227. PMID 25037503.

[5] 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.

[6] Kardon, Tamas; Stroobant, Vincent; Veiga-da-Cunha, Maria; Schaftingen, Emile Van (15 October 2008). "Characterization of mammalian sedoheptulokinase and mechanism of formation of erythritol in sedoheptulokinase deficiency". FEBS Letters. 582 (23–24): 3330–3334. doi:10.1016/j.febslet.2008.08.024. PMID 18775706.

Sedoheptulose

See also

References