Alternatived Products of [ 533-87-9 ]
Product Details of [ 533-87-9 ]
CAS No. : 533-87-9
MDL No. : MFCD00135596
Formula :
C16 H32 O5
Boiling Point : -
Linear Structure Formula : -
InChI Key : -
M.W : 304.42 g/molPubchem ID : -
Synonyms :
Calculated chemistry of [ 533-87-9 ]
Physicochemical Properties
Num. heavy atoms : 21
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.94
Num. rotatable bonds : 15
Num. H-bond acceptors : 5.0
Num. H-bond donors : 4.0
Molar Refractivity : 84.28
TPSA : 97.99 Ų
Pharmacokinetics
GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.4 cm/s
Lipophilicity
Log Po/w (iLOGP) : 2.68
Log Po/w (XLOGP3) : 2.47
Log Po/w (WLOGP) : 2.47
Log Po/w (MLOGP) : 1.63
Log Po/w (SILICOS-IT) : 3.23
Consensus Log Po/w : 2.5
Druglikeness
Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56
Water Solubility
Log S (ESOL) : -2.29
Solubility : 1.55 mg/ml ; 0.00509 mol/l
Class : Soluble
Log S (Ali) : -4.17
Solubility : 0.0205 mg/ml ; 0.0000673 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.88
Solubility : 0.405 mg/ml ; 0.00133 mol/l
Class : Soluble
Medicinal Chemistry
PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.27
Application In Synthesis of [ 533-87-9 ]
* 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.
Upstream synthesis route of [ 533-87-9 ] Downstream synthetic route of [ 533-87-9 ]
1
[ 533-87-9 ]
[ 2553-17-5 ]
2
[ CAS Unavailable ]
[ 533-87-9 ]
Yield Reaction Conditions Operation in experiment
With silver(I) acetate; acetic acid Erwaermen des Reaktionsprodukts mit 25prozentiger Kalilauge;
3
[ 1194798-36-1 ]
[ 533-87-9 ]
Yield Reaction Conditions Operation in experiment
With potassium hydroxide Hydrolysis;
With sodium hydroxide Hydrolysis;
Reference：
[1]Mitter; Bose; Sen-Gupta
[Science and Culture, 1942, vol. 8, p. 273][Journal of the Indian Chemical Society, 1944, vol. 21, p. 296][Chem.Abstr., 1943, p. 4689]
[2]Mitter; Bose; Sen-Gupta
[Science and Culture, 1942, vol. 8, p. 273][Journal of the Indian Chemical Society, 1944, vol. 21, p. 296][Chem.Abstr., 1943, p. 4689]
4
[ 18951-79-6 ]
[ 533-87-9 ]
Yield Reaction Conditions Operation in experiment
With formic acid; dihydrogen peroxide
5
[ 17941-34-3 ]
[ 533-87-9 ]
Yield Reaction Conditions Operation in experiment
(i) aq. HCl, (ii) aq. NaOH; Multistep reaction;
With potassium hydroxide; hydrogen bromide; acetic acid Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: PhCO2 H, HC(OEt)3 / (heating)
2: aq. H2 O2 , HCO2 H
Reference：
[1]Chatterjea,J.N. et al.
[Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1976, vol. 14, p. 220 - 222]
[2]Sarkar, P. C.; Agarwal, S. C.
[Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 12, p. 1080 - 1082]
[3]Singh,A.N. et al.
[Tetrahedron, 1978, vol. 34, p. 595 - 598]
6
[ 533-87-9 ]
[ 1619-68-7 ]
Yield Reaction Conditions Operation in experiment
90%
With orthoformic acid triethyl ester; benzoic acid for 5h; Heating;
88%
With orthoformic acid triethyl ester; benzoic acid Heating;
With orthoformic acid triethyl ester; benzoic acid (heating);
0.56 g
With phosphonium iodide; acetic acid
Reference：
[1]Subramanian; Sharma
[Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 7, p. 551 - 555]
[2]Sarkar, P. C.; Agarwal, S. C.
[Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 12, p. 1080 - 1082]
[3]Singh,A.N. et al.
[Tetrahedron, 1978, vol. 34, p. 595 - 598]
[4]Majee, R. N.; Ramani, R.
[Journal of the Indian Chemical Society, 1993, vol. 70, # 2, p. 167 - 168]
7
[ 533-87-9 ]
(9R,10S)-9,10-Dihydroxy-16-iodo-hexadecanoic acid methyl ester
[ No CAS ]
(9R,10S)-9,10,16-Trihydroxy-hexadecanoic acid (7S,8R)-7,8-dihydroxy-15-methoxycarbonyl-pentadecyl ester
[ No CAS ]
8
[ 533-87-9 ]
(7S,8R)-7,8-Dihydroxy-hexadecanedioic acid
[ No CAS ]
9
[ 533-87-9 ]
[ 108-24-7 ]
[ 61668-05-1 ]
Yield Reaction Conditions Operation in experiment
With pyridine for 8h; Heating;
10
[ 57491-55-1 ]
[ 533-87-9 ]
Yield Reaction Conditions Operation in experiment
94%
With sodium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;
11
[ 533-87-9 ]
[ 22054-13-3 ]
[ 2553-17-5 ]
12
[ 533-87-9 ]
[ 68373-00-2 ]
Yield Reaction Conditions Operation in experiment
With acetic acid at 80 - 100℃; β-form;
13
[ 533-87-9 ]
[ 1125-88-8 ]
[ 500776-65-8 ]
Yield Reaction Conditions Operation in experiment
With toluene-4-sulfonic acid
14
[ 533-87-9 ]
[ 53837-83-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 88 percent / triethyl orthoformate, benzoic acid / Heating
2: 80 percent / BF3 *Et2 O / 0.25 h / Heating
15
[ 533-87-9 ]
[ 57491-60-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 88 percent / triethyl orthoformate, benzoic acid / Heating
2: 80 percent / BF3 *Et2 O / 0.25 h / Heating
3: 91 percent / pyridine / 0.75 h / Heating
16
[ 533-87-9 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 88 percent / triethyl orthoformate, benzoic acid / Heating
2: 80 percent / BF3 *Et2 O / 0.25 h / Heating
3: 91 percent / pyridine / 0.75 h / Heating
4: AlCl3 , Br2 , NaN3 , CH3 CN / 6 h / Ambient temperature
17
[ 533-87-9 ]
[ 57491-64-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 0.56 g / phosphonium iodide, AcOH
2: 0.51 g / pyridine / 15 h / -5 °C
3: 0.30 g / NaI / acetone / 16 h / Heating
18
[ 533-87-9 ]
[ 373-49-9 ]
19
[ 533-87-9 ]
[ 1120-25-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 0.56 g / phosphonium iodide, AcOH
2: 0.51 g / pyridine / 15 h / -5 °C
3: 0.30 g / NaI / acetone / 16 h / Heating
4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C
5: 0.19 g / conc. H2 SO4 / 6 h / Heating
20
[ 533-87-9 ]
[ 34010-20-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: 0.56 g / phosphonium iodide, AcOH
2: 0.51 g / pyridine / 15 h / -5 °C
3: 0.30 g / NaI / acetone / 16 h / Heating
4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C
5: 0.19 g / conc. H2 SO4 / 6 h / Heating
6: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature
7: 0.1 g / pyridine / 25 h / Ambient temperature
21
[ 533-87-9 ]
[ 57491-62-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 0.56 g / phosphonium iodide, AcOH
2: 0.51 g / pyridine / 15 h / -5 °C
22
[ 533-87-9 ]
[ 10378-01-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 0.56 g / phosphonium iodide, AcOH
2: 0.51 g / pyridine / 15 h / -5 °C
3: 0.30 g / NaI / acetone / 16 h / Heating
4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C
5: 0.19 g / conc. H2 SO4 / 6 h / Heating
6: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature
23
[ 533-87-9 ]
[ 40642-43-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
5: conc. H2 SO4 / Heating
6: 92 percent / pyridine / 20 h / -5 °C
7: 80 percent / zinc (dust), NaI / 2.5 h / Heating
8: 85 percent / LAH / tetrahydrofuran / 4 h / Heating
24
[ 533-87-9 ]
[ 16974-10-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 9 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
5: conc. H2 SO4 / Heating
6: 92 percent / pyridine / 20 h / -5 °C
7: 80 percent / zinc (dust), NaI / 2.5 h / Heating
8: 85 percent / LAH / tetrahydrofuran / 4 h / Heating
9: 90 percent / pyridine / 8 h / Ambient temperature
25
[ 533-87-9 ]
[ 49592-98-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
5: conc. H2 SO4 / Heating
6: 92 percent / pyridine / 20 h / -5 °C
7: 80 percent / zinc (dust), NaI / 2.5 h / Heating
26
[ 533-87-9 ]
[ 83005-39-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
5: 95 percent / conc. H2 SO4 / 6 h / Heating
6: pyridine
7: 88 percent / zinc, NaI / Heating
27
[ 533-87-9 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
Multi-step reaction with 2 steps
1: acetylation
2: 1) cupric acetate, pyridine, 2) lead tetraacetate / benzene / 1) room temperature, 2) reflux
Reference：
[1]Subramanian, G. B. V.; Sharma, Rajiv
[Synthetic Communications, 1989, vol. 19, # 7,8, p. 1197 - 1202]
[2]Subramanian; Sharma
[Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 7, p. 551 - 555]
28
[ 533-87-9 ]
[ 86244-69-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
29
[ 533-87-9 ]
[ 125043-79-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
5: conc. H2 SO4 / Heating
30
[ 533-87-9 ]
[ 125043-77-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
31
[ 533-87-9 ]
[ 125043-81-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
5: 95 percent / conc. H2 SO4 / 6 h / Heating
32
[ 533-87-9 ]
[ 125043-78-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: conc. H2 SO4 / 6 h / Heating
33
[ 533-87-9 ]
[ 125043-80-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
5: conc. H2 SO4 / Heating
6: 92 percent / pyridine / 20 h / -5 °C
34
[ 533-87-9 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: pyridine / 8 h / Heating
2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating
3: 1.) KMnO4 , adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h
4: 92 percent / triethyl orthoformate, benzoic acid / Heating
5: 95 percent / conc. H2 SO4 / 6 h / Heating
6: pyridine
35
[ 533-87-9 ]
[ 35507-71-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 90 percent / triethyl orthoformate, benzoic acid / 5 h / Heating
2: 94 percent / pyridine / 12 h / Ambient temperature
3: cupric acetate, pyridine, lead tetraacetate / benzene / 1) 30 min, 2) reflux, 2 h
4: 93 percent / NaOH / methanol; H2 O / 6 h / Heating
5: 92 percent / pyridine / 20 h / -5 °C
6: 86 percent / NaI, zinc dust / 1,2-dimethoxy-ethane / 3 h / Heating
36
[ 533-87-9 ]
[ 93416-10-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: acetylation
2: 1) cupric acetate, pyridine, 2) lead tetraacetate / benzene / 1) room temperature, 2) reflux
3: 6percent aqueous alkali / methanol / Heating
4: 1) acetoxyborohydride, 2) H2 O2 , NaOH
37
[ 533-87-9 ]
[ 124395-02-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 90 percent / triethyl orthoformate, benzoic acid / 5 h / Heating
2: 94 percent / pyridine / 12 h / Ambient temperature
3: cupric acetate, pyridine, lead tetraacetate / benzene / 1) 30 min, 2) reflux, 2 h
4: 93 percent / NaOH / methanol; H2 O / 6 h / Heating
38
[ 533-87-9 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: acetylation
2: 1) cupric acetate, pyridine, 2) lead tetraacetate / benzene / 1) room temperature, 2) reflux
3: 6percent aqueous alkali / methanol / Heating
39
[ 533-87-9 ]
[ 124395-01-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 90 percent / triethyl orthoformate, benzoic acid / 5 h / Heating
2: 94 percent / pyridine / 12 h / Ambient temperature
3: cupric acetate, pyridine, lead tetraacetate / benzene / 1) 30 min, 2) reflux, 2 h
40
[ 533-87-9 ]
[ 120537-39-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 90 percent / triethyl orthoformate, benzoic acid / 5 h / Heating
2: 94 percent / pyridine / 12 h / Ambient temperature
41
[ 533-87-9 ]
[ 124395-03-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 90 percent / triethyl orthoformate, benzoic acid / 5 h / Heating
2: 94 percent / pyridine / 12 h / Ambient temperature
3: cupric acetate, pyridine, lead tetraacetate / benzene / 1) 30 min, 2) reflux, 2 h
4: 93 percent / NaOH / methanol; H2 O / 6 h / Heating
5: 92 percent / pyridine / 20 h / -5 °C
42
[ 533-87-9 ]
[ 57491-57-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: methanol; diethyl ether
2: Py / CH2 Cl2 / 0 °C
43
[ 533-87-9 ]
(7S,8R)-7,8-Dibromo-hexadecanedioic acid
[ No CAS ]
44
[ 533-87-9 ]
(7S,8R)-7,8-Dihydroxy-hexadecanedioic acid dimethyl ester
[ No CAS ]
45
[ 533-87-9 ]
[ 68326-26-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: PhCO2 H, HC(OEt)3 / (heating)
2: Ambient temperature
46
[ 533-87-9 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: PhCO2 H, HC(OEt)3 / (heating)
2: Ambient temperature
3: (i) (COCl)2, Py, benzene, (ii) /BRN= 6125709/, Py
47
[ 64-17-5 ]
[ 533-87-9 ]
[ 6003-09-4 ]
Yield Reaction Conditions Operation in experiment
71%
With sulfuric acid for 2h; Reflux;
48
[ 533-87-9 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: sulfuric acid / 2 h / Reflux
2: VinP4 polyketide synthase thioesterase domain / dimethyl sulfoxide / 24 h / 28 °C / pH 7 / aq. phosphate buffer; Enzymatic reaction
49
[ 533-87-9 ]
[ 2553-17-5 ]
50
[ 533-87-9 ]
[ 18951-79-6 ]
Yield Reaction Conditions Operation in experiment
92%
With 1H-imidazole; iodine; chloro-diphenylphosphine In 1,4-dioxane; toluene for 4h;
51
[ 533-87-9 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 1H-imidazole; iodine; chloro-diphenylphosphine / 1,4-dioxane; toluene / 4 h
2: boron trifluoride diethyl etherate / 0.5 h / Heating
3: magnesium(II) chloride hexahydrate / 220 - 320 °C
52
[ 533-87-9 ]
[ 2553-17-5 ]
53
[ 533-87-9 ]
[ 82342-32-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: sodium hydroxide; sodium periodate / water; chloroform / 0.5 h / 40 °C
2: pyridine / Heating
54
[ 533-87-9 ]
[ 135276-33-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: sodium hydroxide; sodium periodate / water; chloroform / 0.5 h / 40 °C
2: pyridine / Heating
3: boron trifluoride diethyl etherate / 0.25 h / Heating
55
[ 533-87-9 ]
[ 78924-81-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 1H-imidazole; iodine; chloro-diphenylphosphine / 1,4-dioxane; toluene / 4 h
2: boron trifluoride diethyl etherate / 0.5 h / Heating
56
[ 533-87-9 ]
[ 22054-13-3 ]
[ 2553-17-5 ]
57
[ 533-87-9 ]
[ 2553-17-5 ]
58
[ 533-87-9 ]
C15 H30 O3
[ No CAS ]
59
[ 533-87-9 ]
[ 101-70-2 ]
[ 2414486-22-7 ]
Yield Reaction Conditions Operation in experiment
54%
With di-tert-butyl peroxide; copper(II) hexafluoroacetylacetonate; 9-mesitylacridine In ethyl acetate at 35℃; for 36h; Inert atmosphere; Irradiation;
Reference：
[1]Arman, Hadi D.; Dang, Hang T.; Haug, Graham C.; Larionov, Oleg V.; Nguyen, Viet D.; Nguyen, Vu T.; Vuong, Ngan T. H.
[Angewandte Chemie - International Edition, 2020, vol. 59, # 20, p. 7921 - 7927][Angew. Chem., 2020, vol. 132, # 20, p. 7995 - 8001,7]
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