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17311

Sigma-Aldrich

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:
69-65-8
Molecular Weight:
182.17
Beilstein:
1721898
EC Number:
200-711-8
MDL number:
MFCD00064287
UNSPSC Code:
12352201
PubChem Substance ID:
329751528
NACRES:
NA.22

Agency

USP/NF
tested according to Ph. Eur.

Quality Level

200

Assay

≥97%

form

powder

mp

167-170 °C (lit.)

solubility

water: soluble(lit.)

SMILES string

OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO

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

InChI key

FBPFZTCFMRRESA-KVTDHHQDSA-N

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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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK4501
BCCH2534
BCCF7539
BCCD7832
BCCC4766

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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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