Home Cart Sign in  
Chemical Structure| 488-23-3 Chemical Structure| 488-23-3

Structure of 1,2,3,4-Tetramethylbenzene
CAS No.: 488-23-3

Chemical Structure| 488-23-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Amarawan Intasiri ; Siena E. Illa ; Supadach Prertprawnon ; Shenghong Wang ; Li Li ; Thomas W. Bell , et al.

Abstract: The parallel artificial membrane permeability assay (PAMPA) is widely used for estimating biomembrane permeabilities of experimental drugs in . However, there are few reports of studies using PAMPA to measure membrane permeabilities of chemicals of environmental concern (CECs) outside the pharmaceutical domain, many of which differ substantially from drugs in their physicochemical properties. We applied PAMPA methods simulating gastrointestinal (PAMPA-GIT) and blood-brain barrier (PAMPA-BBB) membranes under consistent conditions to 51 CECs, including some pharmaceuticals. A backward stepwise multivariate linear regression was implemented to explore the correlation between the differences of measured permeabilities from PAMPA-GIT and PAMPA-BBB and Abraham solute descriptors. In addition, a previously reported in silico model was evaluated by comparing predicted and measured permeability results. PAMPA-GIT and PAMPA-BBB experimental permeability results agreed relatively well. The backward stepwise multivariate linear regression identified excess molar refraction and polarizability to be significant at the 0.10 level in predicting the differences between PAMPA-GIT and PAMPA-BBB. The in silico model performed well – with predicted permeability of most compounds within two-fold of experimentally measured values. We found that CECs pose experimental challenges to the PAMPA method in terms of having lower solubility and lower stability compared to most drugs.

Keywords: PAMPA ; Blood-brain barrier ; Gastrointestinal tract ; Permeability ; Chemicals of environmental concern

Purchased from AmBeed:

Alternative Products

Product Details of [ 488-23-3 ]

CAS No. :488-23-3
Formula : C10H14
M.W : 134.22
SMILES Code : CC1=CC=C(C)C(C)=C1C
MDL No. :MFCD00008521
InChI Key :UOHMMEJUHBCKEE-UHFFFAOYSA-N
Pubchem ID :10263

Safety of [ 488-23-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 488-23-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 46.31
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.42
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

4.0
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.92
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

4.47
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.72
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.51

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.64
Solubility 0.031 mg/ml ; 0.000231 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.7
Solubility 0.0267 mg/ml ; 0.000199 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.91
Solubility 0.0164 mg/ml ; 0.000122 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.28 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.0

Application In Synthesis of [ 488-23-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 488-23-3 ]

[ 488-23-3 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 488-23-3 ]
  • [ 40101-36-8 ]
  • [ 36321-73-0 ]
  • 3
  • [ 36321-73-0 ]
  • [ 10034-85-2 ]
  • red phosphorus [ No CAS ]
  • [ 488-23-3 ]
  • 4
  • [ 381-98-6 ]
  • [ 488-23-3 ]
  • [ 1219921-42-2 ]
  • 5
  • [ 16957-70-3 ]
  • [ 488-23-3 ]
  • 3-ethyl-2,4,5,6,7-pentamethyl-2,3-dihydro-1H-inden-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% One equivalent of oxalyl chloride (26.5 g, 208 mmol) was addedto a 2 L reaction vessel containing one equivalent of (E)-<strong>[16957-70-3]2-methylpent-2-enoic acid</strong> (23.9 g, 208 mmol) in DCM (500 mL) under aflow of N2. While stirring, five drops of dry DMF were added intothe mixture resulting in effervescence. The reaction mixture wasleft stirring for 2 h. Then, the reaction was cooled to 8 C andallowed to equilibrate. 1.1 equivalents of aluminium trichloride(30.6 g, 230 mmol) was added, under a flow of N2, to the reactor.The reaction mixture changed in colour from a pale yellow to adeep orange almost instantly. 0.9 equivalents of 1,2,3,4-tetramethylbenzene(25.0 g, 176 mmol) was diluted in DCM (100 mL)and transferred to an addition funnel. This mixture was added tothe reaction vessel dropwise over 15 min where a colour changefrom deep orange to blood red was observed. The solution wasthen left to stir for 4 h, after which a 1:1 mixture of conc. HCland ice (200 mL) was added slowly to quench the reaction. Thereaction mixture changed colour from blood red to a light orangeduring this work-up. The product was extracted with DCM(3 100 mL) and the combined organic layers were washed withdeionised water (3 100 mL) before being dried using anhydrousMgSO4. This was filtered and the DCM solvent was removed in vacuo to afford (3-EtInd)O as a beige solid in 100percent yield (41.8 g,214 mmol). Colourless crystals suitable for a single crystal X-raydiffraction study were grown from a hexanes solution at 5 C. 1HNMR (400 MHz, CDCl3, 25C): d (ppm) 0.56 (t, 3H, 3JHH = 7.5 Hz,Me), 1.27 (d, 3H, 3JHH = 7.2 Hz, Me), 1.763 (m, 2H, CH2), 2.23 (s,3H, Ar-Me), 2.28 (s, 3H, Ar-Me), 2.28 (s, 3H, Ar-Me), 2.62 (s, 3H,Ar-Me), 2.74 (dq, 1H, 3JHH = 7.2 Hz, CH), 3.45 (m, 1H, CH). 13C{1H}NMR (101 MHz, CDCl3, 25 C): d (ppm) 9.9 (Me), 11.0 (Me), 13.8(Ar-Me), 15.2 (Ar?Me), 15.4 (Ar-Me), 16.8 (Ar-Me), 23.9 (CH2),41.4 (CH), 48.1 (CH), 130.1 (Ar), 131.1 (Ar), 133.4 (Ar), 134.9 (Ar),141.4 (Ar), 152.7 (Ar), 209.7 (CO). MS (ESI): Calculated231.17434; Found: 231.17446. CHN Anal. (percent): Expected: C 83.43,H 9.63; Found: C 83.53, H 9.75. IR (cm1): 1691.52 (COstretching). X-ray parameters: C16H22O, M = 230.33 g/mol,Triclinic, P1, a = 5.2601(2) A, b = 8.7982(3) A, c = 15.0482(6) A,a = 74.690(1), b = 85.558(2), c = 78.454(2), V = 657.89(4) A3,Z = 2, l = 0.07 mm1, R = 0.056 and CCDC number: 1472636.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 488-23-3 ]

Aryls

Chemical Structure| 700-12-9

A777498 [700-12-9]

1,2,3,4,5-Pentamethylbenzene

Similarity: 1.00

Chemical Structure| 620-14-4

A492333 [620-14-4]

3-Ethyltoluene

Similarity: 0.94

Chemical Structure| 934-80-5

A715007 [934-80-5]

4-Ethyl-1,2-dimethylbenzene

Similarity: 0.94

Chemical Structure| 103-29-7

A695765 [103-29-7]

1,2-Diphenylethane

Similarity: 0.88

Chemical Structure| 612-71-5

A991287 [612-71-5]

1,3,5-Triphenylbenzene

Similarity: 0.88