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Ergosterol

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Name

Ergosterol

EINECS 200-352-7
CAS No. 57-87-4 Density 1 g/cm3
PSA 20.23000 LogP 7.33080
Solubility PRACTICALLY INSOLUBLE Melting Point 156-158 °C(lit.)
Formula C28H44O Boiling Point 501.5 °C at 760 mmHg
Molecular Weight 396.657 Flash Point 216.3 °C
Transport Information UN 2811 6.1/PG 2 Appearance white to yellow crystalline powder
Safety 28-36/37-45 Risk Codes 28-48/20/22-40-38
Molecular Structure Molecular Structure of 57-87-4 (Ergosterol) Hazard Symbols VeryT+
Synonyms

Ergosterol (8CI);(22E,24R)-Ergosta-5,7,22-trien-3b-ol;(24R)-Ergosta-5,7,22-trien-3b-ol;24-Methylcholesta-5,7,22-trien-3b-ol;24R-Methylcholesta-5,7,22E-trien-3b-ol;24a-Methyl-22E-dehydrocholesterol;3b-Hydroxyergosta-5,7,22-triene;Ergosterin;Provitamin D2;Reishi Mushroom PE;

Article Data 33

Ergosterol Synthetic route

C42H61N3O6S*C6H15N

57-87-4

Ergosterol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 16h; Heating;76%
28421-56-9

3β-acetoxy-5α,8α-(4-phenyl-1,2,4-triazolidine-3,5-dione-1,2-diyl)ergosta-6,22-diene

A

57-87-4

Ergosterol

B

1-Isobutyl-4-phenyl-[1,2,4]triazolidin-3-one

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane; toluene at 0℃; for 0.166667h;A 70%
B n/a
10123-90-7

3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene

A

57-87-4

Ergosterol

B

1-Isobutyl-4-phenyl-[1,2,4]triazolidin-3-one

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane; toluene at 0℃; for 0.166667h;A 51%
B n/a
131321-88-5

(24R)-5,7-Ergostadiene-1α,3β,25-triol

57-87-4

Ergosterol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 0.05h; Irradiation;25%
60-29-7

diethyl ether

21307-05-1

previtamin D2

A

57-87-4

Ergosterol

B

474-69-1

lumisterol

C

115-61-7

tachysterol

Conditions
ConditionsYield
at 0℃; UV-Licht.Irradiation;
17398-57-1

(22E,24R)-ergosta-4,7,22-triene-3-one

57-87-4

Ergosterol

Conditions
ConditionsYield
With aluminum isopropoxide; isopropyl alcohol
19044-12-3

lanosterol

57-87-4

Ergosterol

Conditions
ConditionsYield
biosynthesis by Botrytis cinerea in the presence of (dl)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol;
87530-75-4

benzoyloxy-3β (urazolo-1',2')-5α,8α ergostadiene-6,22

57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;10 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;10 % Turnov.
87530-76-5

benzoyloxy-3β (benzalamino-4' urazolo-1',2')-5α,8α ergostadiene-6,22

57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;53 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;53 % Turnov.
87530-79-8

benzoyloxy-3β (p-nitrophenyl-4' urazolo-1',2')-5α,8α ergostadiene-6,22

57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;98 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;98 % Turnov.

Ergosterol Standards and Recommendations

ASSAY OF Ergosterol: 90.0% min
OPTICAL ROTATION: -122° ~ -132° (C=1.2 in CHCl3)

Ergosterol Specification

The CAS registry number of Ergosterol is 57-87-4. Its EINECS registry number is 200-352-7. The IUPAC name is (3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol. In addition, the molecular formula is C28H44O and the molecular weight is 396.65. What's more, it is a biological precursor (a provitamin) to vitamin D2 and belongs to the classes of Pharmaceutical Intermediates; Steroids; Biochemistry; Hydroxysteroids; Vitamins; Vitamins and derivatives.

Physical properties about this chemical are: (1)ACD/LogP: 9.30; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 1; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 9.23 Å2; (7)Index of Refraction: 1.542; (8)Molar Refractivity: 124.19 cm3; (9)Molar Volume: 394 cm3; (10)Polarizability: 49.23 ×10-24cm3; (11)Surface Tension: 38.9 dyne/cm; (12)Density: 1 g/cm3; (13)Flash Point: 216.3 °C; (14)Enthalpy of Vaporization: 88.71 kJ/mol; (15)Boiling Point: 501.5 °C at 760 mmHg; (16)Vapour Pressure: 3.7E-12 mmHg at 25°C.

Preparation of Ergosterol: Ergosterol is present in cell membranes of fungi yet absent in those of animals. And it is also present in the cell membranes of some protists, such as trypanosomes. In addition, it can be extracted from yeast. And it also can be extracted from tobacco.

Uses of Ergosterol: it can be used in biochemical research and used as an indicator of fungal biomass in soil. And it can be used to get ergosterone. This reaction will need reagent aluminum triisopropoxide and solvents toluene and cyclohexanone. The reaction time is 20 minutes by heating. The yield is about 75%.

Ergosterol can be used to get ergosterone

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to the skin and very toxic if swallowed. There is limited evidence of a carcinogenic effect . And it has danger of serious damage to health by prolonged exposure through inhalation and if swallowed. When you are using it, wear suitable protective clothing and gloves. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer). In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@@]3(C)CC4
(2)InChI: InChI=1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
(3)InChIKey: DNVPQKQSNYMLRS-APGDWVJJBI

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