42822-86-6|2-(2-Hydroxypropan-2-yl)-5-methylcyclohexanol| Ambeed

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Quality Control of [ 42822-86-6 ] Purity: 95% SDS Specification

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Product Details of [ 42822-86-6 ]

CAS No. :	42822-86-6
Formula :	C₁₀H₂₀O₂
M.W :	172.26
SMILES Code :	OC1C(CCC(C1)C)C(O)(C)C
MDL No. :	MFCD12756283
InChI Key :	LMXFTMYMHGYJEI-UHFFFAOYSA-N
Pubchem ID :	556998

Safety of [ 42822-86-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 42822-86-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	50.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	40.46 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.35
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.17
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.55
Log P_o/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.	1.52
Log P_o/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	1.28
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.78

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.21
Solubility	1.06 mg/ml ; 0.00618 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.	-2.65
Solubility	0.383 mg/ml ; 0.00223 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	-0.91
Solubility	21.1 mg/ml ; 0.123 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	High
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	No
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.	-5.81 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	0.0
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	1.0
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<1.0
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)	2.91

Application In Synthesis of [ 42822-86-6 ]

* 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 [ 42822-86-6 ]

[ 42822-86-6 ] Synthesis Path-Downstream 1~32

1
[ 64-18-6 ]
[ 2385-77-5 ]
[ 42822-86-6 ]
[ 89-79-2 ]

References: [1]Chemisches Zentralblatt,1917,vol. 88,p. 289.

2
[ 2385-77-5 ]
[ 42822-86-6 ]

References: [1]Memoirs of the College of Science, Kyoto Imperial University,vol. <A> 11,p. 182.
Chemisches Zentralblatt,1928,vol. 99,p. 1326.
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1928,vol. 187,p. 272.
Bulletin de la Societe Chimique de France,1929,vol. <4>45,p. 809.
[3]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1897,vol. 124,p. 1309.
[4]Chemisches Zentralblatt,1917,vol. 88,p. 289.

3
[ 42822-86-6 ]
[ 89-79-2 ]
[ 859181-11-6 ]

References: [1]Memoirs of the College of Science, Kyoto Imperial University,vol. <A> 11,p. 193,195.
Chemisches Zentralblatt,1928,vol. 99,p. 1326.

4
[ 89-79-2 ]
[ 42822-86-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1908,vol. 360,p. 91.
Justus Liebigs Annalen der Chemie,1918,vol. 414,p. 209.
Chemisches Zentralblatt,1915,vol. 86,p. 824.

5
[ 42822-86-6 ]
[ 108-24-7 ]
[ 89-49-6 ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1897,vol. 124,p. 1309.

6
[ 42822-86-6 ]
[ 64-19-7 ]
3-acetoxy-8-chloro-<i>p</i>-menthane [ No CAS ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1897,vol. 124,p. 1309.

7
[ 31750-21-7 ]
[ 42822-86-6 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 1548 - 1553.

8
[ 42822-86-6 ]
[ 3304-24-3 ]

References: [1]Journal of Agricultural and Food Chemistry,1996,vol. 44,p. 1829 - 1832.

9
[ 13834-13-4 ]
[ 42822-86-6 ]

References: [1]Journal of Agricultural and Food Chemistry,1996,vol. 44,p. 1829 - 1832.

10
[ 7647-01-0 ]
[ 2385-77-5 ]
[ 42822-86-6 ]

References: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1938,vol. 254,p. 139,142.

11
[ 2385-77-5 ]
[ 7732-18-5 ]
[ 42822-86-6 ]

References: [1]Industrial and Engineering Chemistry,1948,vol. 40,p. 258,259.
[2]Industrial and Engineering Chemistry,1948,vol. 40,p. 258,259.

12
[ 2385-77-5 ]
[ 7664-93-9 ]
[ 42822-86-6 ]
[ 89-79-2 ]

References: [1],vol. 11,p. 175,181.
Chemisches Zentralblatt,1928,vol. 99,p. 1326.

13
[ 7664-93-9 ]
[ 42822-86-6 ]
[ 89-79-2 ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1928,vol. 187,p. 272.
Bulletin de la Societe Chimique de France,1929,vol. <4>45,p. 809.

Yield	Reaction Conditions	Operation in experiment
		(3) After 155 g (969 mMol) of 25% sodium hydroxide aqueous solution was added in the reaction product (the reaction liquid) obtained by the above-mentioned process (1) to make the liquid alkali (pH 12), 700 g of toluene was added and the extraction treatment of the reaction liquid was conducted under stirring. After being separated and recovered from water phase, the organic phase was washed with 600 g of water and separated. Then, the washed organic phase was concentrated under reduced pressure and 536 g of crude para-menthane-3,8-diol was obtained. Next, said crude para-menthane-3,8-diol was distilled and375.8 g of purified para-menthane-3,8-diol (a mixture of cis form and trans form) was obtained.

15
dextrorotatory citronellal [ No CAS ]
[ 42822-86-6 ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1897,vol. 124,p. 1309.

16
<i>p</i>-menthane-3,8-diyldiamine [ No CAS ]
[ 7732-18-5 ]
[ 7782-77-6 ]
[ 42822-86-6 ]

References: [1]Chemische Berichte,1905,vol. 38,p. 147.

17
[ 106-23-0 ]
2-[2,6-dimethyl-5-heptenyl]-4,4,8-trimethylhexahydro-1,3-benzodioxine [ No CAS ]
[ 42822-86-6 ]
[ 89-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid;cetyltrimethylammonim bromide; In water; at 35℃; for 5.0h;	A method for carrying out this invention is as indicated below. The actual detail of the processing will be known to those skilled in the art:1. A solution of hexadecyltrimethylammonium bromide (0.05%) in 5% sulphuric was charged into a reactor and vigorously stirred. Citronellal in an amount equivalent to 33.32.% of the total charge was fed into the reactor over a five hour period with the temperature being maintained at or below 350C. Stirring was continued for a further three hours.2. The stirring was stopped and the two phases were allowed to separate. The lower aqueous acid solution was run off to be used in further batches. The temperature should be maintained above 30C for ease of separation. <n="15"/>3. The organic layer was washed with a solution of mild alkali such as sodium carbonate or sodium bicarbonate to remove residual acid until an aliquot shaken with water showed a pH of 5.0 - 8.0. The product was filtered through a lOOmuM filter to remove residual water and any suspended solids.4. The resultant product is a clear or slightly opaque almost colourless, moderately viscous liquid with a slight pleasant floral odour quite unlike that of the starting material.Analysis of the product of the above process shows a typical composition: PMD-citronellal acetal 5-12%Isopulegole 7-14%/?alphara-menthane-3,8-diol remainder

References: [1]Patent: WO2009/34352,2009,A1 .Location in patent: Page/Page column 13-14.

18
[ 106-23-0 ]
2-[2,6-dimethyl-5-heptenyl]-4,4,8-trimethylhexahydro-1,3-benzodioxine [ No CAS ]
[ 529-02-2 ]
[ 42822-86-6 ]

Yield	Reaction Conditions	Operation in experiment
<= 7%; <= 10%; 90%	sulfuric acid; In water; at 60℃; for 7.0h;	A bench-scale PMD synthesis reaction was carried out using a 500 ml jacketed glass reactor, a heated feed vessel, and an over-head stirrer fitted with a four-blade stainless steel impeller, thermometer and two integral baffles. The reactor temperature was set to a temperature of 60 deg C by circulating heating fluid, kept at the desired constant temperature (+/- 0.5 deg C) in a constant temperature bath. Dilute sulphuric acid (14Og of a 0.53% (m/m) solution 0.00757mol) was added to the reactor and allowed to equilibrate to the desired reaction temperature. Citronellal (30.08g; 0.193mol), pre-heated to the desired reaction temperature, was added to the reactor drop-wise over a period of 60 minutes, while the reactor was agitated at a stirring rate of 2000 rpm. The reaction was allowed to proceed for a further 6 hours following completion of the citronellal addition step.Once the reaction had stopped, the reactor contents were drained into a separating funnel and allowed to settle for 1 minute after which the aqueous phase was drained off. The organic phase was washed with 5Og of a 2.5% (w/v) solution of NaHCO3 to remove any residual sulphuric acid catalyst. The mixture was allowed to settle for approximately 2 minutes after which the bottom aqueous phase was drained off.Residual water was removed from the organic phase on a rotary evaporator. The crude product was then distilled under vacuum (1 15 deg C and 8 mBar) to recover citronellal and pulegol. The desired product PMD was recovered as a thick viscous liquid from the bottom of the still and analyzed by means of gas chromatography. In different embodiments, the yield of PMD varied between 80 - 90 % and typically contained up to about 10 % of pulegol, up to about 7% PMD-acetal and about 2- 5% of un-reacted citronellal.

References: [1]Patent: WO2009/135229,2009,A1 .Location in patent: Page/Page column 14.

Yield	Reaction Conditions	Operation in experiment
	In hexane; at -18℃; for 24.0h;Purification / work up;	For example 50, 1 part by mass of n-hexane was added to 4 parts of the crude product from a batch synthesis reactor after phase separation and the mixture thoroughly mixed. The mixture was cooled to -18 0C for 24 hours which results in the formation of an opaque-white solid product which was filtered under vacuum and washed once with 50 ml ice cold n-hexane before drying in air at 8O0C. The results obtained for this recrystallisation study are summarised in Table 4.For example 51 , a sample of crude product obtained following vacuum evaporation of unreacted citronellal and pulegol intermediate was treated in the same manner as described above. The resultant filter cake was washed twice with cold solvent. The results obtained are summarised in Table 4.

20
[ 106-23-0 ]
[ 42822-86-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sulfuric acid; In water; at 100℃; for 4.0h;Green chemistry;	Citronellal (30.08 g, 0.193 mol) was added into stirred dilutesulphuric acid (140 g, 0.0076 mol of a 0.3% (v/v)) solution at atemperature of 100 C. After 4 hour of stirring the aqueousphase was separated from the organic oil phase. The organicphase was neutralised with 50 mL of 2.5% (v/v) sodium hydrogen carbonate (NaHCO3) solution to remove the remains ofsulphuric acid catalyst and dried (MgSO4). The product was recrystallized from n-hexane at -18 C for 24 hours. p-Menthane-3,8-diol (3) was obtained as white crystals (96%). 1H NMR(400 MHz, CDCl3, ppm) delta0.80-0.96 (m, 3H), 0.89-0.90 (m,1H), 0.99-1.03 (m, 2H), 1.11-1.19 (m, 3H), 1.33 (s, 3H),1.66-1.68 (m, 2H), 1.72-1.82 (m, 3H), 3.40 (s, 2H) and 4.38(br s, 1H); 13C NMR(100 MHz, CDCl3, ppm) delta20.2, 22.1,25.5, 28.6, 29.9, 34.8, 42.4, 49.2, 67.7 and 73.2; FTIR (cm-1):3220, 2941, 2911, 1158 and 931; m/z(CI) 172 (M+, 1), 157 (9),139 (20), 96 (50), 81 (100) and 59 (90); GC tR= 15.0 min.
	sulfuric acid; In water; at 90℃; for 0.5h;Product distribution / selectivity;	The experiment described in Example 1 was repeated several times with slight modifications in the reaction temperature, amount of catalyst used, and the ratio of the aqueous catalyst phase relative to the organic citronellal phase as indicated in Table 1. In all of the examples of Table 1 , the citronellal starting material was added in a single batch to the pre-heated aqueous catalyst mixture, and the reaction was allowed to proceed for only 30 minutes before the reaction was stopped and worked up as described for Example 1. The results obtained for these experiments, namely the amount of citronellal (mmol), amount of PMD (mmol), and amount of PMD-acetal (mmol) are summarised in Table 1.
64.2 g	With sulfuric acid; water; In toluene; at 70℃; for 11.0h;	Example 2 Synthesis of (IRS)-p-Menthane-3,8-diol Isomer Mixture By using 77.1 g of dl-citronellal (manufactured by Takasago International Corporation) containing 50% by mass of d-citronellal and 50% by mass of 1-citronellal as a raw material, 64.2 g of a (1RS)-p-menthane-3,8-diol isomer mixture was obtained by the same synthetic method as in [Example 1]. In this isomer mixture, (1R)-isomers accounted for 50% by mass of the entire composition, and (1S)-isomers accounted for 50% by mass of the entire composition (more specifically, the (1S,3R,4S) isomer accounted for 33% by mass of the entire composition, and the (1R,3S,4R) isomer accounted for 33% by mass of the entire composition).

References: [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2046 - 2054.
[2]Patent: WO2009/135229,2009,A1 .Location in patent: Page/Page column 15.
[3]Journal of the American Chemical Society,2012,vol. 134,p. 17873 - 17876.
[4]Patent: US2014/219931,2014,A1 .Location in patent: Paragraph 0076; 0077.

21
[ 106-23-0 ]
p-menthane-3,8-diol citronellal acetal [ No CAS ]
[ 42822-86-6 ]
[ 89-79-2 ]

References: [1]Green Chemistry,2009,vol. 11,p. 1227 - 1231.

22
[ 106-23-0 ]
2-[2,6-dimethyl-5-heptenyl]-4,4,8-trimethylhexahydro-1,3-benzodioxine [ No CAS ]
[ 42822-86-6 ]
[ 89-79-2 ]
[ 89-79-2 ]
[ 89-79-2 ]
[ 89-79-2 ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 17873 - 17876.

23
[ 2051-49-2 ]
[ 42822-86-6 ]
C₂₂H₄₀O₄ [ No CAS ]