Ergosterol
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MedKoo CAT#: 600135

CAS#: 57-87-4

Description: Ergosterol is a sterol found in fungi, and named for ergot, the common name of members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol does not occur in plant or animal cells; reports of its isolation from plants are generally ascribed to fungal contamination of the plant material from which steroids are being isolated. Ergosterol is a component of yeast and other fungal cell membranes, serving many of the same functions that cholesterol serves in animal cells. Ergosterol is provitamin form of vitamin D2; natural ultraviolet (UV) irradiation of ergosterol, isolated or in situ, results in vitamin D2 production that can contribute to satisfying human dietary vitamin D requirements. (Source: http://en.wikipedia.org/wiki/Ergosterol).

Chemical Structure

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Ergosterol
CAS# 57-87-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 600135
Name: Ergosterol
CAS#: 57-87-4
Chemical Formula: C28H44O
Exact Mass: 396.34
Molecular Weight: 396.650
Elemental Analysis: C, 84.79; H, 11.18; O, 4.03

Price and Availability

Size Price Availability Quantity
5g USD 350 2 weeks
25g USD 650 2 weeks
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Synonym: Ergosterol; Provitamin D; Provitamin D2.

IUPAC/Chemical Name: (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

InChi Key: DNVPQKQSNYMLRS-APGDWVJJSA-N

InChi Code: InChI=1S/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

SMILES Code: O[C@H]1CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H]([C@@H](/C=C/[C@H](C)C(C)C)C)CC[C@@]4([H])C3=CC=C2C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.
In vitro activity: ER (Ergosterol) significantly increased the protein expression of Nrf2 and HO-1 in chondrocytes in a dose-dependent manner (Fig. 1C and D). Nuclear protein was extracted for assays and the results showed that ER upregulated nuclear Nrf2 expression (Fig. 1E). ER treatment caused a significant increase in luciferase activity (Fig. 1F), which indicated that ER activated the HO-1 promoter transactivation activity. Reference: Exp Ther Med. 2021 Mar; 21(3): 194. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7812583/
In vivo activity: The number of Con A-dependent aggregates was significantly higher in the carcinogenic group than that in the control group. In contrast, the number of cell aggregates was significantly lower in rats treated with ergosterol compared to the carcinogenesis group (Table 2). Reference: Biomedicines. 2020 Jul; 8(7): 180. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7400612/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 2.0 5.04
Ethanol 1.6 3.91
Ethanol:PBS (pH 7.2) (1:2) 0.3 0.76

Preparing Stock Solutions

The following data is based on the product molecular weight 396.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Cai D, Yan H, Liu J, Chen S, Jiang L, Wang X, Qin J. Ergosterol limits osteoarthritis development and progression through activation of Nrf2 signaling. Exp Ther Med. 2021 Mar;21(3):194. doi: 10.3892/etm.2021.9627. Epub 2021 Jan 8. PMID: 33488803; PMCID: PMC7812583. 2. Sun X, Liu Y, Feng X, Li C, Li S, Zhao Z. The key role of macrophage depolarization in the treatment of COPD with ergosterol both in vitro and in vivo. Int Immunopharmacol. 2020 Feb;79:106086. doi: 10.1016/j.intimp.2019.106086. Epub 2019 Dec 23. PMID: 31874368. 3. Ikarashi N, Hoshino M, Ono T, Toda T, Yazawa Y, Sugiyama K. A Mechanism by which Ergosterol Inhibits the Promotion of Bladder Carcinogenesis in Rats. Biomedicines. 2020 Jun 27;8(7):180. doi: 10.3390/biomedicines8070180. PMID: 32605038; PMCID: PMC7400612. 4. Yazawa Y, Ikarashi N, Hoshino M, Kikkawa H, Sakuma F, Sugiyama K. Inhibitory effect of ergosterol on bladder carcinogenesis is due to androgen signaling inhibition by brassicasterol, a metabolite of ergosterol. J Nat Med. 2020 Sep;74(4):680-688. doi: 10.1007/s11418-020-01419-4. Epub 2020 Jun 1. PMID: 32488609.
In vitro protocol: 1. Cai D, Yan H, Liu J, Chen S, Jiang L, Wang X, Qin J. Ergosterol limits osteoarthritis development and progression through activation of Nrf2 signaling. Exp Ther Med. 2021 Mar;21(3):194. doi: 10.3892/etm.2021.9627. Epub 2021 Jan 8. PMID: 33488803; PMCID: PMC7812583. 2. Sun X, Liu Y, Feng X, Li C, Li S, Zhao Z. The key role of macrophage depolarization in the treatment of COPD with ergosterol both in vitro and in vivo. Int Immunopharmacol. 2020 Feb;79:106086. doi: 10.1016/j.intimp.2019.106086. Epub 2019 Dec 23. PMID: 31874368.
In vivo protocol: 1. Ikarashi N, Hoshino M, Ono T, Toda T, Yazawa Y, Sugiyama K. A Mechanism by which Ergosterol Inhibits the Promotion of Bladder Carcinogenesis in Rats. Biomedicines. 2020 Jun 27;8(7):180. doi: 10.3390/biomedicines8070180. PMID: 32605038; PMCID: PMC7400612. 2. Yazawa Y, Ikarashi N, Hoshino M, Kikkawa H, Sakuma F, Sugiyama K. Inhibitory effect of ergosterol on bladder carcinogenesis is due to androgen signaling inhibition by brassicasterol, a metabolite of ergosterol. J Nat Med. 2020 Sep;74(4):680-688. doi: 10.1007/s11418-020-01419-4. Epub 2020 Jun 1. PMID: 32488609.

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1: Zhang YQ, Rao R. Beyond ergosterol: linking pH to antifungal mechanisms. Virulence. 2010 Nov-Dec;1(6):551-4. Epub 2010 Nov 1. Review. PubMed PMID: 21178501.