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[ CAS No. 5957-80-2 ] {[proInfo.proName]}

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Chemical Structure| 5957-80-2
Chemical Structure| 5957-80-2
Structure of 5957-80-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 5957-80-2 ]

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Product Details of [ 5957-80-2 ]

CAS No. :5957-80-2 MDL No. :MFCD02752467
Formula : C20H26O4 Boiling Point : -
Linear Structure Formula :- InChI Key :XUSYGBPHQBWGAD-PJSUUKDQSA-N
M.W : 330.42 Pubchem ID :442009
Synonyms :
NSC 39143
Chemical Name :(4aR,9S,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-2,3,4,9,10,10a-hexahydro-1H-9,4a-(epoxymethano)phenanthren-12-one

Calculated chemistry of [ 5957-80-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.65
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 92.83
TPSA : 66.76 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.93
Log Po/w (XLOGP3) : 4.38
Log Po/w (WLOGP) : 3.96
Log Po/w (MLOGP) : 3.25
Log Po/w (SILICOS-IT) : 4.05
Consensus Log Po/w : 3.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.77
Solubility : 0.00565 mg/ml ; 0.0000171 mol/l
Class : Moderately soluble
Log S (Ali) : -5.5
Solubility : 0.00105 mg/ml ; 0.00000317 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.45
Solubility : 0.0116 mg/ml ; 0.0000352 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.88

Safety of [ 5957-80-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5957-80-2 ]

* 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 [ 5957-80-2 ]

[ 5957-80-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 5957-80-2 ]
  • columbaridione [ No CAS ]
  • 2
  • [ 5957-80-2 ]
  • [ 108-24-7 ]
  • 11,12-diacetyl-carnosol [ No CAS ]
YieldReaction ConditionsOperation in experiment
92.5% With pyridine; dmap; triethylamine; In dichloromethane; at 20℃; To a solution of <strong>[5957-80-2]carnosol</strong> (2) (50 mg) in pyridine (1.5 ml), acetic anhydride (3.0 ml) was added and the mixture was allowed to stand at room9temperature overnight. The reaction mixture was worked up in the usual manner, to afford <strong>[5957-80-2]carnosol</strong> diacetate (92.5 %).11,12-diacetyl-<strong>[5957-80-2]carnosol</strong> (16). Isolated as an amorphous solid, mp: 158-159C. 1H-NMR (300 MHz, CDCl3) 0.86 (3H, s, Me-19), 0.91 (3H, s, Me-18), 1.19 and 1.20 (each 3H, d, J = 7.0 Hz, Me-16 and Me-17), 2.29 (3H, s, Ar-OAc), 2.30 (3H, s, Ar-OAc), 2.67 (lH, bd, J = 10.0 Hz, H-1beta), 2.90 (1H, hept, J = 7.0 Hz, H-15), 5.50 (1H, dd, J1 = 1.4 Hz, J2 = 4.0 Hz, H-7), 7.10 (1H, s, H-14); EIMS m/z (%) 414 [M]+ (10), 354 (50), 327 (10), 286 (100), 228 (19), 202 (8), 69 (55) 55 (100).
  • 3
  • [ 5957-80-2 ]
  • [ 74-88-4 ]
  • [ 25460-12-2 ]
  • [ 85514-25-6 ]
  • 4
  • [ 5957-80-2 ]
  • [ 74-88-4 ]
  • [ 25460-12-2 ]
  • [ 85514-25-6 ]
  • (4aR,10aS)-5-Hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-1,3,4,10a-tetrahydro-2H-phenanthrene-4a-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; at 20℃; for 24.0h;Product distribution / selectivity; EXAMPLE 2; 1Og rosemary extract of Commercailly available rosemary extract A (43% carnosic acid, 18% <strong>[5957-80-2]carnosol</strong>) was stirred in 40 ml acetic acid for Id at ambient. The slurry was filtered and the crystals washed with 8 ml of acetic acid. The crystals where dried in the vacuum at 700C. We obtained 1.96g <strong>[5957-80-2]carnosol</strong> of 78% purity (yield = 83% ); EXAMPLE 3; Examples 3a-3b where conducted similar to example 2
  • 6
  • [ 5957-80-2 ]
  • [ 450410-87-4 ]
YieldReaction ConditionsOperation in experiment
93.5% With silver(l) oxide; In diethyl ether; for 2.0h; General procedure: Freshly prepared Ag2O (2 eq) was added to a solution of <strong>[5957-80-2]carnosol</strong> (2) or rosmanol (3) in diethyl ether (5 mL). After being stirred for 2 h, the solution was filtered, the solvent was evaporated and the product was chromatographed over silica gel using CH2Cl2 as eluent to yield <strong>[5957-80-2]carnosol</strong> quinone (13) (93.5 %) or rosmaquinone (14) (99%) respectively.<strong>[5957-80-2]Carnosol</strong> quinone (13). 1H-NMR (300 MHz, CDCl3) 0.87 (3H, s, Me-19), 0.89 (3H, s, Me-18), 1.12 (6H, d, J = 7.0 Hz, Me-16 y Me-17), 1.23 (1H, m, H-3alpha), 1.53 (1H, bd, J = 13.3 Hz, H-3beta), 1.65 (2H, overlap, H-2 and H-5), 1.87 (1H, dt, H-2alpha), 1.97 (1H, m, H-6beta), 2.20 (1H, m, H-6alpha), 2.30 (1H, td, J1 = 4.6 Hz, J2 = 14.0 Hz, H-1alpha), 2.68 (1H, bd, J = 14.4 Hz, H-1beta), 2.97 (1H, hept, J = 7.0 Hz, H-15), 5.19, 5.20 (1H, dd, J1 = 1.4 Hz, J2 = 4.0 Hz, H-7), 6.67 (1H, s, H-14); 13C-NMR (CDCl3) 18.2 (t, C-2), 19.3 (q, C-18), 21.3 (q, C-16), 21.3 (q, C-17), 27.0 (t, C-1), 27.8 (t, C-6), 27.8 (d, C-15), 32.0 (q, C-19), 34.4 (s, C-4), 40.5 (t, C-3), 44.8 (d, C-5), 48.7 (s, C-10), 76.4 (d, C-7), 129.6 (d, C-14), 135.6 (s, C-9), 151.1 (s, C-13), 152.5 (s, C-8), 173.3 (s, C-20), 176.2 (s, C-11), 179.2 (s, C-12); EIMS m/z 328 [M]+ (5), 284 (43), 215 (100), 204 (17), 165 (14), 141 (14), 55 (20).
  • 7
  • [ 5957-80-2 ]
  • [ 475654-77-4 ]
  • 8
  • [ 67-56-1 ]
  • [ 5957-80-2 ]
  • [ 113085-62-4 ]
  • 9
  • [ 5957-80-2 ]
  • [ 64-17-5 ]
  • [ 111200-01-2 ]
  • 12
  • [ 3650-09-7 ]
  • [ 5957-80-2 ]
YieldReaction ConditionsOperation in experiment
Example 3; 13. Ig rosemary extract (containing 43% carnosic acid and 18% carnosol ), 6Og acetic acid and 13 mg of iron(III) chloride hexahydrate where stirred under a nitrogen blanket. At 15C was slowly added 2.9 ml hydrogen peroxide 35% in water. The mixture was stirred for 1.5 h at 15C followed by addition of ImI hydrochloric acid 37%. The mixture was stirred for 18h at ambient. The slurry was filtered and washed with 10 ml acetic acid. The crystallisate was dried in the vacuum at 700C. We obtained 5.57g carnosol of 92% purity. Yield = 65%.
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