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isopropyl beta-D-thiogalactopyranoside

HCID 656894
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
367-93-1
Standard SMILES
CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChIKey
BPHPUYQFMNQIOC-NXRLNHOXSA-N
Molecular formula
C9H18O5S
Average molar mass
238.3 g/mol
Monoisotopic mass
238.08749468

Overview

Isopropyl beta-D-thiogalactopyranoside is an S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.

Names & identifiers

Preferred name
isopropyl beta-D-thiogalactopyranoside
IUPAC
(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol
English name
IPTG
Molecular formula
C9H18O5S
Molecular weight
238.3

Names & synonyms

IPTG367-93-1Isopropyl-beta-D-thiogalactopyranosideIsopropyl beta-D-thiogalactopyranosideISOPROPYL THIOGALACTOSIDEIsopropyl-beta-D-thiogalactosideIsopropyl beta-D-1-thiogalactopyranosideIsopropyl beta-D-thiogalactosideIsopropyl 1-Thio-beta-D-galactopyranosideDTXSID6041052X73VV2246B(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol
Show more names
isopropyl β-d-1-thiogalactopyranosideISOPROPYL-B-D-THIOGALACTOPYRANOSIDEIsopropyl-B-D-thiogalactosideIsopropyl-β-D-thiogalatopyranosideIsopropyl β-D-Thiogalactopyranoside (IPTG)
CHEBI:61448beta-D-Galactopyranoside, 1-methylethyl 1-thio-(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyl-oxane-3,4,5-triolThiogalactoside, Isopropylisopropyl beta-thiogalactosideIsopropyl 1 Thio beta D galactopyranoside1-Thio-beta-D-galactopyranoside, IsopropylRefChem:389084

Database identifiers

Properties

Computed structural properties

XLogP
-0.5
Topological polar surface area
115 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
15
Formal charge
0
Complexity
201

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Biochemical Research
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionWhite solid with an odor of sulfur; [Promega MSDS]

Physicochemical properties

Melting point
105 °C · 105 °C
alpha
-31 · -31 º (c=1, water)
Boiling point
350.9 °C · 350.9°C (rough estimate)
Density
1.3329 · 1.3329 (rough estimate)
refractive index
1.506 · 1.5060 (estimate)
storage temp.
2 · 2-8°C
solubility
Soluble in Water or Methanol.
form
Crystalline Powder
pka
13 · 13.00±0.70(Predicted)
color
White

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 · 5 items

This chemical does not meet GHS hazard criteria for 81% (115 of 142) of all reports.

Warning

H302 (12%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 142 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Isopropyl thiogalactoside: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn eye irritant; Harmful by ingestion; May cause liver and kidney injury; [Promega MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (12%)

Safety data

F
10
wgk
3
tsca
TSCA listed
hs_code
29389090
risk_code
19-40-66-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
hazard_code
Xn,Xi
safety_code
23-24/25-36/37-22-36/37/39-27-26

Chemistry & industry

Uses & manufacturing

UsesUsed to induce protein synthesis and to detect lac gene activity; [Merck Index]
General Manufacturing Information.beta.-D-Galactopyranoside, 1-methylethyl 1-thio-: ACTIVE
Applications · 3 items

DescriptionIPTG (also known as Isopropyl-β-D-Thiogalactopyranoside) is a molecular biology reagent that functions as an inducer of galactosidase activity by binding to and inhibiting the repressor. It is a molecular mimic of allolactose, a lactose metabolite that triggers transcription of the lac operon, and it is therefore used to induce protein expression where the gene is under the control of the lac operator. IPTG cannot be hydrolyzed or broken down by the E. coli therefore the concentration remains constant during cell replication. IPTG is often used at a final concentration ranging from 0.5-1.0 mM. X-Gal is often used with IPTG since it provides an easy visual method to monitor whether protein expression has occurred. X-Gal as the name implies contains a galactose group that once metabolized causes a bright blue color change.

UsesIsopropyl-β-D-thiogalactoside is used as a reagent in molecular biology. It is used as an effective β-galactosidase inducer of protein expression where the gene is under the control of the lac operator. It is used with 5-bromo-4-chloro-3-indolyl-beta-D-galactopyranoside to identify the non-recombinant plasmid in cloning experiments by blue-white screen methodology.

General DescriptionInducer for β-galactosidase, an enzyme that promotes lactose utilization. Use in conjunction with X-Gal. Molecular Biology grade.Stock solutions:X-Gal: 20 mg/ml in DMFIPTG: 20 mg/ml in waterUse 4:1 (X-Gal:IPTG)Assay: ≥99%Dioxane: None detectedMelting point: 110-114°CSpecific rotation [a]25/D (1%, water): -34.0 to -29.0° Intended for laboratory and manufacturing use only. Not for drug, food, or household use.

Preparation methods · 1 item

Related reactions

66 records
New reaction record
HRID 2685 reaction equation
HRID 2685As reactantuspto-grants-1998_03
HRID 215703 reaction equation
HRID 215703As reactantuspto-grants-2012_06
HRID 330728 reaction equation
HRID 330728As reactantuspto-grants-2014_11
HRID 341728 reaction equation
HRID 341728As productuspto-grants-1999_01
HRID 363711 reaction equation
HRID 363711As productuspto-grants-1999_02
HRID 383217 reaction equation
HRID 383217As reactantuspto-grants-2013_02
HRID 399376 reaction equation
HRID 399376As reactantuspto-grants-1998_10
HRID 399377 reaction equation
HRID 399377As reactantuspto-grants-1998_10
Page 1 of 9

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS
367-93-1
PubChem CID
656894
DTXSID
DTXSID6041052
ChEMBL
CHEMBL1233651
ChEBI
CHEBI:61448
UNII
X73VV2246B
EC Number
206-703-0
Nikkaji
J193.883E
PH
5 · 5-7 (50g/L)
biological source
synthetic
Water Solubility
soluble
Merck
14 · 14,5082
BRN
4631 · 4631
Stability
Stable. Incompatible with strong oxidizing agents.
InChI
1S/C9H18O5S/c1-4(2)15-9-8(13)7(12)6(11)5(3-10)14-9/h4-13H,3H2,1-2H3/t5-,6+,7+,8-,9+/m1/s1
InChIKey
BPHPUYQFMNQIOC-NXRLNHOXSA-N
SMILES
S([C@@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)O)O)CO)C(C)C
CAS DataBase Reference
367 · 367-93-1(CAS DataBase Reference)
FDA UNII
73 VV2246B · X73VV2246B
EPA Substance Registry System
Isopropyl .beta.- thiogalactoside (367-93-1)
UNSPSC Code
51171641 · 51171641
NACRES
54 · NA.54
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
319 · H319-H351
Precautionary statements
281 · P281-P305+P351+P338
Hazard Codes
Xn,Xi
Risk Statements
19 · 19-40-66-36/37/38
Safety Statements
23 · 23-24/25-36/37-22-36/37/39-27-26
WGK Germany
3 · 3
F
10 · 10
TSCA
TSCA listed
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids
Storage Class
11 - Combustible Solids
Hazard statements
H319-H351
Precautionary statements
P281-P305+P351+P338

Preparationa synthetic method of isopropyl-β-D-thiogalactoside. The steps are as follows:Step 1: Dissolve β-D-galactose pentaacetate in any organic solvent of methylene chloride, chloroform or 1,2-dichloroethane, and add Lewis acid (boron trifluoride ether, (Aluminum trichloride, zinc chloride) catalyst and potassium ethylxanthate or sodium ethylxanthate are reacted to obtain tetraacetylgalactose ethylxanthate after treatment.Step 2: Dissolve tetraacetyl galactose ethyl xanthate, 2-bromopropane and sodium carbonate in methanol or ethanol at a temperature of 20°C to 80°C and react for 4-6 hours to obtain isopropyl group after treatment Isopropyl-β-D-thiogalactoside.

Upstream & downstream products

Upstream raw materials

D-Galactopyranose pentaacetateD-(+)-GALACTOSE.beta.-D-Galactopyranose(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate2-Propanethiolbeta-D-Galactose pentaacetateMethanolSodium Methoxide

Downstream products

Sarsasapogenin 3-O-β-D-galactopyranosid

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [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]
清宁生物(江苏博泉生物科技有限公司)19352250998 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
南京百芙利科技有限责任公司25-25-58740604 15951658055 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
南京奥生化学技术有限公司+86 (25) 82263158
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
天津万象恒远科技有限公司15722085254 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
泰州凯美迪生物医药技术有限公司0523-86200218 18994667082 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
南京美博生物科技有限公司025-58619198 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
新乡市翌诚生物科技有限公司0373-5799336 18937330588 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
北京泰亚杰科技有限公司021-33690831-8001 13552411790;18616022633 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
张家港保税区凯利特化工有限公司18606289633 15862625988 · [email protected]
上海特伯化学科技有限公司+86-21-60341587 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
上海遐瑞医药科技有限公司+86 21 61551611
南京诺利斯医药科技有限公司13901585132 · [email protected]
上海健超生物科技有限公司150-2103-5486 18017383231 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
无锡中坤生化科技有限公司+86 0510-85629785

Additional notes

DefinitionChEBI: Isopropyl beta-D-thiogalactopyranoside is an S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.