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Merck

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

Key Documents

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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

200

agency

tested according to Ph. Eur.

assay

≥97%

form

powder

mp

167-170 °C (lit.)

solubility

water: soluble(lit.)

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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.

wgk

WGK 1

Storage Class

11 - Combustible Solids

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

17311-VAR-F: + 17311-BULK-F: + 17311-1KG-F:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3245
BCCK4501
BCCH2534
BCCF7539
BCCD7832

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Production Methods of D-Mannitol.
Makkee M, et al.
Starch/Staerke, 37(4), 136-141 (1985)
Polyhydroxylated piperidines and azepanes from D-mannitol synthesis of 1-deoxynojirimycin and analogues.
Poitout L, et al.
Tetrahedron Letters, 35(20), 3293-3296 (1990)
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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