17311
D-Mannitol
tested according to Ph. Eur.
Synonym(s):
Mannitolum, Mannite
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About This Item
Empirical Formula (Hill Notation):
C6H14O6
CAS Number:
Molecular Weight:
182.17
UNSPSC Code:
12352201
NACRES:
NA.22
PubChem Substance ID:
EC Number:
200-711-8
Beilstein/REAXYS Number:
1721898
MDL number:
Product Name
D-Mannitol, tested according to Ph. Eur.
SMILES string
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI key
FBPFZTCFMRRESA-KVTDHHQDSA-N
InChI
1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
Quality Level
agency
tested according to Ph. Eur.
assay
≥97%
form
powder
mp
167-170 °C (lit.)
solubility
water: soluble(lit.)
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Application
D-Mannitol may be used in the preparation of the following:
- D-mannitol and L-iditol bis-epoxides, useful substrates for the synthesis of polyhydroxylated piperidines and azepanes
- chiral hydroxyl monophosphane, [(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethyl-1-phenylphospholane]
- bisphospholanes, [1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethylphospholanyl]benzene] and [1,2-bis[(2S,3S,4S,5S)-2,5-diethyl-3,4-dihydroxyphospholanyl]benzene]
Biochem/physiol Actions
A sugar alcohol sweet tastant. Used in sweetness inhibition studies.
General description
D-Mannitol (Mannite, Mannitolum), an alditol, is an sweet tasting crystalline solid. It is naturally found in manna, olives, mushrooms and celery plants. It has been synthesized from glucose, via catalytic hydrogenation reaction. It is widely used as growth supplement in bacterial cultures.
D-Mannitol is an acyclic carbohydrate. Crystal parameters and space groups of the various polymorphic crystalline forms of mannitol have been reported. It has been proposed as an artificial sweetner. Synthesis of D-mannitol from D-glucose or D-glucose/D-fructose syrups in the presence of glucose isomerase and copper-on-silica has been proposed.
wgk
WGK 1
Storage Class
11 - Combustible Solids
ppe
Eyeshields, Gloves, type N95 (US)
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Polyhydroxylated piperidines and azepanes from D-mannitol synthesis of 1-deoxynojirimycin and analogues.
Poitout L, et al.
Tetrahedron Letters, 35(20), 3293-3296 (1990)
Production Methods of D-Mannitol.
Makkee M, et al.
Starch/Staerke, 37(4), 136-141 (1985)
The crystal structures of the α′- and β- forms of D-mannitol.
Berman HM, et al.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 24(3), 442-449 (1968)
W Li et al.
The Journal of organic chemistry, 65(11), 3489-3496 (2000-06-08)
Chiral hydroxyl monophosphane 3 [(2S,3S,4S,5S)-3,4-dihydroxy-2, 5-dimethyl-1-phenylphospholane] and bisphospholanes 5a [1,2-bis[(2S, 3S,4S,5S)-3,4-dihydroxy-2,5-dimethylphospholanyl]benzene] and 5b [1, 2-bis[(2S,3S,4S,5S)-2,5-diethyl-3,4-dihydroxyphospholanyl]benzene] were synthesized from readily available D-mannitol in high yields. Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate
Eagleson M.
Concise Encyclopedia Chemistry, 622-622 (1994)
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