Lactobionic Acid

HCID 7314
NotesReactions
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Basic information

CAS
96-82-2
Standard SMILES
O=C(O)[C@H](O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO
InChIKey
JYTUSYBCFIZPBE-AMTLMPIISA-N
Molecular formula
C12H22O12
Average molar mass
358.3 g/mol
Monoisotopic mass
358.11112613

Names & identifiers

Preferred name
Lactobionic Acid
IUPAC
(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid
English name
Lactobionic acid
Molecular formula
C12H22O12
Molecular weight
358.3

Names & synonyms

LACTOBIONIC ACID96-82-24-O-beta-D-Galactopyranosyl-D-gluconic acidDTXSID30488614-(beta-D-Galactosido)-D-gluconic acid65R938S4DVDTXCID6028787CHEBI:55481RefChem:798371GlyTouCan:G18874TBG18874TBD-GLUCONIC ACID, 4-O-BETA-D-GALACTOPYRANOSYL-
Show more names
LACTOBIONIC ACID POWDERLactose acidLactobionateLactobionSactobionic acidLaCLobionic AcidLACTOBIONIC ACID 97%
202-538-3MFCD00078147(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acidD-Gluconic acid, 4-O-b-D-galactopyranosyl-C12H22O12D-Gluconic acid, 4-O-.beta.-D-galactopyranosyl-(2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanoic acid(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-hexanoic acid

Database identifiers

CAS
96-82-2
PubChem CID
7314
DTXSID
DTXSID3048861
ChEMBL
CHEMBL3039602
ChEBI
CHEBI:55481
UNII
65R938S4DV
EC Number
202-538-3
Nikkaji
J4.724D

Properties

Computed structural properties

XLogP
-5
Topological polar surface area
218 Ų
Hydrogen bond donors
9
Hydrogen bond acceptors
12
Rotatable bonds
8
Heavy atoms
24

Experimental & physicochemical properties

Collision Cross Section168.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
113 · 113-118 °C(lit.)
alpha
22.8 · 22.8 º (c=10, H2O)
Boiling point
410.75 °C · 410.75°C (rough estimate)
Density
1.4662 · 1.4662 (rough estimate)
refractive index
26 ° · 26 ° (C=8.8, H2O)
storage temp.
Inert atmosphere,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 92.3% (24 of 26) of all reports.

Not Classified；Reported as not meeting GHS hazard criteria by 24 of 26 companies (only 7.7% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 26 reports by companies from 4 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 24 of 26 reports by companies.；There are 2 notifications provided by 2 of 26 reports by companies with hazard statement code(s).；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. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationD-Gluconic acid, 4-O-.beta.-D-galactopyranosyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesNot Classified

Regulatory information

Regulatory InformationD-Gluconic acid, 4-O-.beta.-D-galactopyranosyl-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
1
hs_code
29400000
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >25；Consumption (g per capita; approx.) in Germany (2009): 0.000305；Calculated removal (%): 92.1
Applications · 5 items

DescriptionLactobionic acid (C12H22O12) is a disaccharide obtained from the oxidation of lactose. Chemically, Lactobionic acid is made up of a galactose moiety that is bonded to a gluconic acid molecule through an ether-like bond. The compound can be dehydrated to a lactone. Lactobionic acid is widely used in the chemical, food and pharmaceutical industries due to its chelating, emulsifying, humectant and chelating properties. Lactobionic acid and its constituent salts are essential as food additives due to excellent solubility, good taste, and health-promoting aspects. The compound may also be essential in the synthesis of targetable and biocompatible drug delivery systems.

UsesLactobionic acid is mainly used in preservation solutions for organ transplantation. It is used to produce erythromycine lactobionate.

Usesfood additive

UsesArginine metabolite in bovine brain; clonidine-displacing substance activity

UsesAn inhibitor of matrix metalloproteinases

Preparation methods · 1 item

PreparationThe selective transformation of lactose into Lactobionic acid entails the oxidation of the radical aldehyde category of glucose on the lactose molecule to the carboxylic classification. The production of Lactobionic acid entails various processes which may include enzymatic synthesis, microbial production, biocatalytic oxidation, electrochemical oxidation and heterogeneous catalytic oxidation.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]

Additional notes

DefinitionChEBI: A disaccharide formed between beta-D-galactose and D-gluconic acid.

Related reactions

3 records
New reaction record

Compound notes

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