Sucrose

Sucrose
Haworth projection of sucrose
Ball-and-stick model of sucrose
Names
IUPAC name
β-D-Fructofuranosyl α-D-glucopyranoside
Systematic IUPAC name
(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-Dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
  • Sugar;
  • Saccharose;
  • α-D-glucopyranosyl-(1→2)-β-D-fructofuranoside;
  • β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside;
  • β-(2S,3S,4S,5R)-fructofuranosyl-α-(1R,2R,3S,4S,5R)-glucopyranoside;
  • α-(1R,2R,3S,4S,5R)-glucopyranosyl-β-(2S,3S,4S,5R)-fructofuranoside;
  • Dodecacarbon monodecahydrate;
  • ((2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxapent-2-yl]oxy-6-(hydroxymethyl)oxahexane-3,4,5-triol)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.304 Edit this at Wikidata
EC Number
  • 200-334-9
KEGG
RTECS number
  • WN6500000
UNII
  • InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1 checkY
    Key: CZMRCDWAGMRECN-UGDNZRGBSA-N checkY
  • InChI=1/C12H22O11/c13-1-4-6(16)8(18)9(264115619)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1
  • O1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O[C@@]2(O[C@@H]([C@@H](O)[C@@H]2O)CO)CO
Properties[1]
C
12H
22O
11
Molar mass 342.30 g/mol
Appearance Colourless crystals or white powder
Density 1.587 g/cm3 (0.0573 lb/cu in), solid
Melting point None; decomposes at 186 °C (367 °F; 459 K)
2.01 g/mL (20 °C (68 °F))
log P −3.76
Structure
Monoclinic
P21
Thermochemistry
−2,226.1 kJ/mol (−532.1 kcal/mol)[2]
1,349.6 kcal/mol (5,647 kJ/mol)[3] (Higher heating value)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Lethal dose or concentration (LD, LC):
29700 mg/kg (oral, rat)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)[4]
REL (Recommended)
 TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)[4]
IDLH (Immediate danger)
 N.D.[4]
Safety data sheet (SDS) ICSC 1507
Related compounds
Related compounds
 Lactose
Maltose
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula C
12H
22O
11.

For human consumption, sucrose is extracted and refined from either sugarcane or sugar beet. Sugar mills – typically located in tropical regions near where sugarcane is grown – crush the cane and produce raw sugar which is shipped to other factories for refining into pure sucrose. Sugar beet factories are located in temperate climates where the beet is grown, and process the beets directly into refined sugar. The sugar-refining process involves washing the raw sugar crystals before dissolving them into a sugar syrup which is filtered and then passed over carbon to remove any residual colour. The sugar syrup is then concentrated by boiling under a vacuum and crystallized as the final purification process to produce crystals of pure sucrose that are clear, odorless, and sweet.

Sugar is often an added ingredient in food production and recipes. About 185 million tonnes of sugar were produced worldwide in 2017.

Sucrose is particularly dangerous as a risk factor for tooth decay because Streptococcus mutans bacteria convert it into a sticky, extracellular, dextran-based polysaccharide that allows them to cohere, forming plaque. Sucrose is the only sugar that bacteria can use to form this sticky polysaccharide.

  1. ^ Sucrose, International Chemical Safety Card 1507, Geneva: International Programme on Chemical Safety, November 2003
  2. ^ Haynes, W. M.; Lide, David R.; Bruno, Thomas J., eds. (2014–2015). CRC Handbook of Chemistry and Physics (95th ed.). CRC Press. pp. 5–40. ISBN 978-1482208672.
  3. ^ CRC Handbook of Chemistry and Physics, 49th edition, 1968–1969, p. D-188.
  4. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0574". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ "57-50-1 - CZMRCDWAGMRECN-UGDNZRGBSA-N - Sucrose [JAN:NF]". ChemIDplus. Archived from the original on 2014-08-12. Retrieved 2014-08-10.