Sucrose

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
CAS Number	57-50-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17992 ;
ChEMBL	ChEMBL253582 ;
ChemSpider	5768 ;
DrugBank	DB02772 ;
ECHA InfoCard	100.000.304
EC Number	200-334-9;
IUPHAR/BPS	5411;
KEGG	C00089;
PubChem CID	5988;
RTECS number	WN6500000;
UNII	C151H8M554 ;
CompTox Dashboard (EPA)	DTXSID2021288 ;
	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 Key: CZMRCDWAGMRECN-UGDNZRGBSA-N ; 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;
	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	C; 12H; 22O; 11
Molar mass	342.30 g/mol
Appearance	white solid
Density	1.587 g/cm3 (0.0573 lb/cu in), solid
Melting point	None; decomposes at 186 °C (367 °F; 459 K)
Solubility in water	~200 g/dL (25 °C (77 °F))
log P	−3.76
Structure
Crystal structure	Monoclinic
Space group	P21
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−2,226.1 kJ/mol (−532.1 kcal/mol)
Std enthalpy of; combustion (ΔcH⦵298)	1,349.6 kcal/mol (5,647 kJ/mol) (Higher heating value)
Hazards
NFPA 704 (fire diamond)	0 1 0
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	29700 mg/kg (oral, rat)
	NIOSH (US health exposure limits):
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.
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). verify (what is ?) Infobox references

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.^[6]

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.^[7]

^ Sucrose, International Chemical Safety Card 1507, Geneva: International Programme on Chemical Safety, November 2003
^ 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.
^ CRC Handbook of Chemistry and Physics, 49th edition, 1968–1969, p. D-188.
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0574". National Institute for Occupational Safety and Health (NIOSH).
^ "57-50-1 - CZMRCDWAGMRECN-UGDNZRGBSA-N - Sucrose [JAN:NF]". ChemIDplus. Archived from the original on 2014-08-12. Retrieved 2014-08-10.
^ Marcy Nicholson (17 November 2017). "World 2017/18 sugar production, consumption seen at record: USDA". Reuters. Archived from the original on 14 September 2019. Retrieved 21 December 2019.
^ Ryan KJ, Ray CG, eds. (2004). Sherris Medical Microbiology (4th ed.). McGraw Hill. ISBN 978-0-8385-8529-0.

[ICSC-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.

[CRC-3] CRC Handbook of Chemistry and Physics, 49th edition, 1968–1969, p. D-188.

[PGCH-4] 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.

[prod2017-6] Marcy Nicholson (17 November 2017). "World 2017/18 sugar production, consumption seen at record: USDA". Reuters. Archived from the original on 14 September 2019. Retrieved 21 December 2019.

[Sherris-7] Ryan KJ, Ray CG, eds. (2004). Sherris Medical Microbiology (4th ed.). McGraw Hill. ISBN 978-0-8385-8529-0.

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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
CAS Number	57-50-1^Y
3D model (JSmol)	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
KEGG	C00089
PubChem CID	5988
RTECS number	WN6500000
UNII	C151H8M554^Y
CompTox Dashboard (EPA)	DTXSID2021288
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(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
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^[1]
Chemical formula	C ₁₂H ₂₂O ₁₁
Molar mass	342.30 g/mol
Appearance	white solid
Density	1.587 g/cm³ (0.0573 lb/cu in), solid
Melting point	None; decomposes at 186 °C (367 °F; 459 K)
Solubility in water	~200 g/dL (25 °C (77 °F))
log P	−3.76
Structure
Crystal structure	Monoclinic
Space group	P2₁
Thermochemistry
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−2,226.1 kJ/mol (−532.1 kcal/mol)^[2]
Std enthalpy of combustion (Δ_cH^⦵₂₉₈)	1,349.6 kcal/mol (5,647 kJ/mol)^[3] (Higher heating value)
Hazards
NFPA 704 (fire diamond)	0 1 0
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	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). Y verify (what is ^YN ?) Infobox references