Name: Ergosterol
SKU: 57-87-4

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Basic Information

Molecular Structure:
CAS No.:	57-87-4
Name:	Ergosterol

Formula:	C₂₈H₄₄O
Molecular Weight:	396.657
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;
EINECS:	200-352-7
Density:	1 g/cm³
Melting Point:	156-158 °C(lit.)
Boiling Point:	501.5 °C at 760 mmHg
Flash Point:	216.3 °C
Solubility:	PRACTICALLY INSOLUBLE
Appearance:	white to yellow crystalline powder
Hazard Symbols:	T+
Risk Codes:	28-48/20/22-40-38
Safety:	28-36/37-45
Transport Information:	UN 2811 6.1/PG 2
PSA:	20.23000
LogP:	7.33080

Synthetic route

: C42H61N3O6S*C6H15N

: 57-87-4
Ergosterol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
at 0℃; UV-Licht.Irradiation;

...Expand

: 17398-57-1
(22E,24R)-ergosta-4,7,22-triene-3-one

: 57-87-4
Ergosterol

Conditions

Conditions	Yield
With aluminum isopropoxide; isopropyl alcohol

: 19044-12-3
lanosterol

: 57-87-4
Ergosterol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

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Standards and Recommendations

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

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

57-87-4

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Standards and Recommendations

Specification