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Biotin hydrazide

HCID 83872
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
66640-86-6
Standard SMILES
NNC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21
InChIKey
KOZWHQPRAOJMBN-ZKWXMUAHSA-N
Molecular formula
C10H18N4O2S
Average molar mass
258.34 g/mol
Monoisotopic mass
258.115047

Overview

structure given in first source; RN given refers to (3aS-(3aalpha,4beta,6aalpha))-isomer

Names & identifiers

Preferred name
Biotin hydrazide
IUPAC
5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanehydrazide
English name
BIOTIN HYDRAZIDE
Molecular formula
C10H18N4O2S
Molecular weight
258.34

Names & synonyms

Biotin hydrazide66640-86-6BD4VQ48JNVDTXSID509852171H-Thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, hydrazide, (3aS-(3aalpha,4beta,6aalpha))-RefChem:119869DTXCID101412415613-970-0biotin-hydrazide(+)-Biotin hydrazide5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanehydrazideMFCD00078532
Show more names
Biotin-Hzbiotin N2H3CAS_66640-86-65-((3aS,4S,6aR)BIOTIN-HydrazidBiontin-Hydrazide
(+)-Biotin-hydrazide5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanehydrazideAS-740835-[(3as,4s,6ar)-2-oxohexahydro-1h-thieno[3,4-d]imidazol-4-yl]pentanehydrazide1H-Thieno[3,4-d]imidazole-4-pentanoic acid, hexahydro-2-oxo-,hydrazide, (3aS,4S,6aR)-5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanehydrazideBiotin-NHNH2Biotin hydrazide HCl

Database identifiers

CAS
66640-86-6

Properties

Computed structural propertiesFilling in

XLogP
-0.7
Topological polar surface area
122 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
17
Formal charge
0
Complexity
313

Physicochemical properties

Melting point
245 · 245-247 °C
Boiling point
633.1 · 633.1±40.0 °C(Predicted)
Density
1.243 · 1.243±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
20 mg/mL · DMSO: ≤20 mg/mL
form
powder
pka
13.25 · 13.25±0.35(Predicted)
color
White to Almost white
BRN
28347 · 28347
InChI
InChI=1S/C10H18N4O2S/c11-14-8(15)4-2-1-3-7-9-6(5-17-7)12-10(16)13-9/h6-7,9H,1-5,11H2,(H,14,15)(H2,12,13,16)/t6-,7-,9-/m0/s1
InChIKey
KOZWHQPRAOJMBN-ZKWXMUAHSA-N
SMILES
C1(=O)N[C@]2([H])[C@H](CCCCC(NN)=O)SC[C@]2([H])N1
CAS DataBase Reference
66640 · 66640-86-6(CAS DataBase Reference)
FDA UNII
4 VQ48JNV · BD4VQ48JNV
UNSPSC Code
12352203 · 12352203

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F
10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29349990
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 5 items

DescriptionBiotin hydrazide is a biotinyl derivative used to label surface functional groups, antibodies, lectins, sugars, nucleic acids, or molecules with free carboxylic or keto groups. Biotin hydrazide is used as a probe for determining protein carbonylation, an irreversible posttranslational modification resulting from the actions of reactive oxygen species or lipid oxidation products. The reaction of this probe is direct and does not require catalysts or reducing agents.

UsesBiotin Hydrazide is a carbohydrate reactive biotinylation reagent used predominately for labeling monoclonal antibodies, unpaired cytosine residues in nucleic acids and glycoproteins.

Usesaldehyde reactive biotinylation reagent

Uses(+)-Biotin hydrazide has been used:the modification of alginatefor the labelling of mitochondrial proteins from non-muscle tissues as a component of glycoprotein staining solutionin periodic acid-biotin-hydrazide (PABH) assay for mucinsfor labeling surface functional groups, biologically active molecules such as antibodies, lectins, sugars, nucleic acids or molecules with free carboxylic or keto groups.for coupling to glycoproteins through the carbohydrate by hydrazone formation

General DescriptionBiotin hydrazide is a biotinylation reagent used to biotinylate glycoproteins with their sugar moieties. Biotin hydrazide can be used to prepare biotin-conjugated alginate. It can also be used for covalent attachment to PAAc via carbodi-imide cross linking.

Related reactions

1 records
New reaction record
HRID 1371254 reaction equation
HRID 1371254As reactantuspto-grants-2007_01

Compound notes

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PubChem CID
83872
DTXSID
DTXSID50985217
ChEMBL
CHEMBL4458159
UNII
BD4VQ48JNV
EC Number
613-970-0
Nikkaji
J851.206J
NACRES
46 · NA.46
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
24 · 24/25
WGK Germany
3 · 3
F
10 · 10
HS Code
29349990 · 29349990
Storage Class
11 · 11 - Combustible Solids