Sucrose

Sucrose

Names
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
CAS Number	57-50-1 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17992 Y
ChEMBL	ChEMBL253582 Y
ChemSpider	5768 Y
DrugBank	DB02772 Y
ECHA InfoCard	100.000.304
EC Number	200-334-9
IUPHAR/BPS	5411
PubChem	5988
RTECS number	WN6500000
UNII	C151H8M554 Y
InChI 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 Y Key: CZMRCDWAGMRECN-UGDNZRGBSA-N Y InChI=1/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
SMILES 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
Chemical formula	C12H22O11
Molar mass	342.30 g/mol
Appearance	white solid
Density	1.587 g/cm3, solid
Melting point	None; decomposes at 186 °C (367 °F; 459 K)
Solubility in water	2100 g/L (25 °C)
log P	−3.76
Chiral rotation ([α]D)	+66.47°
Magnetic susceptibility (χ)	-189.1·10−6 cm3/mol
Structure
Crystal structure	Monoclinic
Space group	P21
Thermochemistry
Std enthalpy of combustion (ΔcHo298)	5,643 kilojoules per mole (1,349 kcal/mol) (3.94 kcal/g)
Hazards
Safety data sheet	ICSC 1507
NFPA 704	1 0 0
Lethal dose or concentration (LD, LC):
LD50 (median dose)	29700 mg/kg (oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)
REL (Recommended)	TWA 10 mg/m3 (total) TWA 5 mg/m3 (resp)
IDLH (Immediate danger)	N.D.
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).
Y  (what is YN ?)
Infobox references

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;

Sucrose is a common, naturally occurring saccharide found in many plants and plant parts. Saccharose is an obsolete name for sugars in general, especially sucrose. The molecule is a disaccharide combination of the monosaccharides glucose and fructose with the formula C₁₂H₂₂O₁₁.

Sucrose is often extracted and refined from either cane or beet sugar for human consumption. Modern industrial sugar refinement processes often involve bleaching and crystallization, producing a white, odorless, crystalline powder with a sweet taste of pure sucrose. This refined form of sucrose is commonly referred to as table sugar or just sugar. It plays a central role as an additive in food production and food consumption all over the world. About 175 million metric tons of sucrose were produced worldwide in 2013.

The word "sucrose" was coined in 1857 by the English chemist William Miller from the French sucre ("sugar") and the generic chemical suffix for sugars -ose. The abbreviated term Suc is often used for sucrose in scientific literature.

In sucrose, the components glucose and fructose are linked via an acetal bond between C1 on the glucosyl subunit and C2 on the fructosyl unit. The bond is called a glycosidic linkage. Glucose exists predominantly as two isomeric "pyranoses" (α and β), but only one of these forms links to the fructose. Fructose itself exists as a mixture of "furanoses", each of which having α and β isomers, but only one particular isomer links to the glucosyl unit. What is notable about sucrose is that, unlike most disaccharides, the glycosidic bond is formed between the reducing ends of both glucose and fructose, and not between the reducing end of one and the nonreducing end of the other. This linkage inhibits further bonding to other saccharide units. Since it contains no anomeric hydroxyl groups, it is classified as a non-reducing sugar.