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Home> Encyclopedia >   /  Other Inorganic Salts  /  Pharmaceutical Intermediates  /  Organic Intermediate
Sucrose structure
Sucrose structure

Sucrose

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
CAS No.: 57-50-1
Molecular Weight:342.3
Modify Date.: 2022-10-31 05:25
Introduction: White odorless crystalline or powdery solid. Denser than water. View more+
1. Names and Identifiers
1.1 Name
Sucrose
1.2 Synonyms

amerfand Amerfond D(+)-Sucrose EINECS 200-334-9 Erlotinib-d16 HCl GNE 410 MFCD00006626 Micr Microse SACCHAROSE SACCHARUM SUCROSE CONFECTIONERS SUCROSE SOLUTION SUCROSE STANDARD SUGAR sugar powder Sugartab Surose α-D-Glc-(1→2)-Β-D-Fru

1.3 CAS No.
57-50-1
1.4 CID
5988
1.5 EINECS(EC#)
200-334-9
1.6 Molecular Formula
C12H22O11 (isomer)
1.7 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
1.8 InChkey
CZMRCDWAGMRECN-UGDNZRGBSA-N
1.9 Canonical Smiles
C(C1C(C(C(C(O1)OC2(C(C(C(O2)CO)O)O)CO)O)O)O)O
1.10 Isomers Smiles
C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O
2. Properties
3.1 Density
1.5805
3.1 Melting point
185-187 °C(lit.)
3.1 Boiling point
397.76°C (rough estimate)
3.1 Refractive index
66.5 ° (C=26, H2O)
3.1 Flash Point
697.1 °C at 760 mmHg
3.1 Precise Quality
342.11600
3.1 PSA
189.53000
3.1 logP
-5.39560
3.1 Solubility
H2O: 500?mg/mL
3.2 AnalyticLaboratory Methods
SUGARS & SUGAR PRODUCTS BY POLARIMETRIC METHODS.
3.3 Appearance
white crystals or powder
3.4 Storage
Ambient temperatures.
3.5 Chemical Properties
White or almost white, crystalline powder, or lustrous, colourless or white or almost white crystals.
3.6 Color/Form
Powder
3.7 Decomposition
When heated to decomposition it emits acrid smoke and fumes.
3.8 Heat of Combustion
-1.35X10+6 cal/mol
3.9 Odor
Characteristic caramel
3.10 PH
Soln are neutral to litmus
3.11 Physical
SUCROSE; is a white odorless crystalline or powdery solid. Denser than water;.
3.12 pKa
12.7(at 25℃)
3.13 Water Solubility
1970 g/L (15 oC)
3.14 Spectral Properties
INDEX OF REFRACTION: 1.5376; SADTLER REFERENCE NUMBER: 8659 (IR, PRISM), 563 (IR, GRATING); SPECIFIC OPTICAL ROTATION: +66.37 @ 20 DEG C/D (WATER)
IR: 3335 (Coblentz Society Spectral Collection)
NMR: 6242 (Sadtler Research Laboratories Spectral Collection)
MASS: 4955 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
3.15 Stability
Stable. Combustible. Incompatible with strong oxidizing agents. Hydrolyzed by dilute acids and by invertase.
3.16 StorageTemp
Store at RT.
3.17 Surface Tension
71-75 mN/m @ 1-0.6 mol/l
3. Use and Manufacturing
4.1 Agricultural Uses
is obtained from sugar beet, sugar cane and sweetsorghum. Table sugar is the most common form ofsucrose. It comprises a glucose unit joined to a fructoseunit. Honey consists of sucrose and its hydrolysisproducts. Sucrose, glucose and fructose all exhibit opticalactivity. When sucrose is hydrolyzed, the rotationchanges from right to left. This is called inversion, and anequimolar mixture of glucose and fructose is called invertsugar. The enzyme invertase hydrolyzes sucrose toglucose and fructose. Sugar occurs universally throughout the plantkingdom in fruits, seeds, flowers and roots.
4.2 Definition
ChEBI: Sucrose is a disaccharide formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose.
4.3 General Description
White odorless crystalline or powdery solid. Denser than water.
4.4 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 304 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 290 of 304 companies. For more detailed information, please visit ECHA C&L website

Of the 4 notification(s) provided by 14 of 304 companies with hazard statement code(s):

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
H311 (50%): Toxic in contact with skin [Danger Acute toxicity, dermal]
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
H331 (50%): Toxic if inhaled [Danger Acute toxicity, inhalation]
H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H335 (14.29%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H373 (28.57%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H400 (50%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P311, P312, P314, P321, P322, P330, P332+P313, P361, P362, P363, P391, P403+P233, P405, and P501
4.5 History
Sucrose is the white granulated compound referred to as sugar. Sucrose is a disaccharide made of glucose and fructose. The main sources of sucrose for the production of commercial sugar are sugarcane and sugar beets. Sugarcane is a tall perennial grass of the genus Saccharum native to Southeast Asia and the South Pacifi c. It has been consumed by chewing the stalk in areas where it grows for thousands of years. Sugarcane spread to India where it was processed to extract crude sugar as early as 2,500 years ago. Persian invaders discovered sugar after invading India and the plant and sugar production spread into the Middle East around 600 c.e. Europeans were introduced to sugar around 1100 c.e. when the first crusaders returned with knowledge of the sweet spice and the Arab Empire spread into Spain.The use of sugar beet to obtain sugar began when the German chemist Andreas Sigismund Marggraf (1709 1782) extracted sucrose from sugar beets using alcohol. The amount of sucrose obtained by Marggraf did not warrant commercial use of beets as a sucrose source. During the late 18th century, Franz Karl Archard (1753 1821), a student of Marggraf, selectively bred beets to increase the sucrose content to 5 6% and developed a commercial method to extract sucrose. Sucrose is predominantly associated with the food industry, but it does have industrial uses in other areas. Sucrose fatty acid esters are a mixture of mono, di, and tri esters of sucrose with fatty acids. Th ese are use in cosmetics, shampoos, resins, inks, paper processing, and pesticides. Sucrose benzoate is used as an emulsifi er and in nail polishes. Sucrose has also been used in making glues and treating leather.
4.6 Methods of Manufacturing
Obtained from sugar cane (Saccharum officinarum L, Gramineae) and sugar beet (Beta valgaris L, Chenopodiaceae). Sugar cane contains from 15-20% and sugar beet form 10-17% sucrose;. Structure: Avery et al, J Chem Soc 1927, 2308; Beevers, Cochrane, Proc Roy Soc 190a, 257 (1947).
4.7 Purification Methods
Crystallise D(+)-sucrose from water (solubility: 1g in 0.5mL H2O at 20o, 1g in 0.2mL in boiling H2O). It is soluble in EtOH (0.6%) and MeOH (1%). Sucrose diacetate hexaisobutyrate is purified by melting and, while molten, treated with NaHCO3 and charcoal, then filtered. [Beilstein 17/8 V 399.]
4.8 Usage
Sucrose (C12H22O11) is one of many forms of sugars (carbohydrates) that are importantorganic compounds for maintaining life.
4. Safety and Handling
5.1 Hazard Codes
Xi
5.1 Risk Statements
36/37/38
5.1 Safety Statements
24/25-37/39-26
5.1 Exposure Standards and Regulations
Substance added directly to human food affirmed as generally recognized as safe (GRAS).
5.2 Octanol/Water Partition Coefficient
log Kow = -3.70
5.3 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5.4 RIDADR
NONH for all modes of transport
5.4 Fire Fighting Procedures
Water
5.5 Safety Profile
Mildly toxic by ingestion. An experimental teratogen. Mutation data reported. Vigorous reaction with nitric acid or sulfuric acid (forms carbon monoxide and carbon dioxide). When heated to decomposition it emits acrid smoke and irritating fumes.
5.6 Formulations/Preparations
USEPA/OPP Pesticide Code 000023; Trade Names: None.
Grade: Reagent, USP, technical, refined.
Also sold as syrup .. liquid sugar
5.7 Incompatibilities
Powdered sucrose may be contaminated with traces of heavymetals, which can lead to incompatibility with active ingredients,e.g. ascorbic acid. Sucrose may also be contaminated with sulfitefrom the refining process. With high sulfite content, color changescan occur in sugar-coated tablets; for certain colors used in sugarcoatingthe maximum limit for sulfite content, calculated as sulfur, is1 ppm. In the presence of dilute or concentrated acids, sucrose ishydrolyzed or inverted to dextrose and fructose (invert sugar).Sucrose may attack aluminum closures.
5.8 WGK Germany
2
5.8 RTECS
WN6500000
5.8 Reactivities and Incompatibilities
Oxidizers, sulfuric acid, nitric acid.
5.9 Report

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

5.10 Safety

Mildly toxic by ingestion. An experimental teratogen. Mutation data reported. Vigorous reaction with nitric acid or sulfuric acid (forms carbon monoxide and carbon dioxide). When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Xi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-37/39-26 
S24/25: Avoid contact with skin and eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39: Wear suitable gloves and eye/face protection.

5.11 Specification

 D(+)-Sucrose , its cas register number is 57-50-1. It also can be called alpha-D-Glucopyranosyl beta-D-fructofuranoside ; beta-D-Fructofuranose-(2-1)-alpha-D-glucopyranoside ; Sucrose ; Saccharose ; and alpha-D-Glucopyranosyl beta-D-fructofuranoside . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: Should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. While, it's inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product: Wash mouth out with water. Notes to physician: Treat supportively and symptomatically.
In addition, D(+)-Sucrose (CAS NO.57-50-1) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Carbon monoxide, carbon dioxide.

5.12 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
domestic animals - goat/sheep LDLo oral 40gm/kg (40000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Nutrition Abstracts and Reviews. Vol. 30, Pg. 503, 1960.
mouse LD50 intraperitoneal 14000mg/kg (14000mg/kg)   Pharmaceutical Chemistry Journal Vol. 15, Pg. 139, 1981.
rat LD50 oral 29700mg/kg (29700mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Toxicology and Applied Pharmacology. Vol. 7, Pg. 609, 1965.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
Used for protein purification in sucrose density gradient studiesSucrose is widely utilized in medications to carry a more pleasant taste to indigestible chemicals. It is used in many medical dosage forms such as chewable tablets, syrups, tablets, or glues. Sucrose is mainly used in foods nowadays. The fatty acid esters of sucrose show useful application in transdermal therapeutic systems. Sucrose-gradient centrifugation also plays an important role in the selective isolation of nocardia spp. from soil.
9.1 Usage
Sucrose is widely utilized in medications to carry a more pleasant taste to indigestible chemicals. It is used in many medical dosage forms such as chewable tablets, syrups, tablets, or glues. Sucrose is mainly used in foods nowadays. The fatty acid esters of sucrose show useful application in transdermal therapeutic systems. Sucrose-gradient centrifugation also plays an important role in the selective isolation of nocardia spp. from soil.
9.2 Usage
Sucrose is used to prepare density gradients for cell/organelle separation. In addition, sucrose can be used as a supplement in plant, insect, and bacterial culture media. It can also be used in various enzymatic assays. Sucrose is used in molecular biology for the preparation of density gradients.
10. Computational chemical data
  • Molecular Weight: 342.3g/mol
  • Molecular Formula: C12H22O11
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 342.11621151
  • Monoisotopic Mass: 342.11621151
  • Complexity: 395
  • Rotatable Bond Count: 5
  • Hydrogen Bond Donor Count: 8
  • Hydrogen Bond Acceptor Count: 11
  • Topological Polar Surface Area: 190
  • Heavy Atom Count: 23
  • Defined Atom Stereocenter Count: 9
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceBwPAAAAAAAAAAAAAAAAAAAASAAAAAkAAAAAAAAAAAAAAAAGgAACAAACBSwgAMACAAABgAAAAAAAAAAAAAAAAAAAAAAAAAREAIAAAAiQAAFAAAHAAHAYAwAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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