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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H42O
Molecular Weight 394.6325
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DEHYDROERGOSTEROL

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)C3=CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C

InChI

InChIKey=QSVJYFLQYMVBDR-CMNOFMQQSA-N
InChI=1S/C28H42O/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/h7-10,14,18-20,22,24-25,29H,11-13,15-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1

HIDE SMILES / InChI

Molecular Formula C28H42O
Molecular Weight 394.6325
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 1
Optical Activity UNSPECIFIED

Dehydroergosterol (DHE) is a naturally occurring, fluorescent analog of cholesterol that mimics the properties of cholesterol in cell membranes. It is readily bound by cholesterol-binding proteins and has been used for real-time probing of the sterol environment and to elucidate intracellular sterol trafficking in living organisms. Also was found, that DHE might be helpful in slowing down the deterioration in brain function by inducing a suitable microglial phenotype and might be a valuable preventive tool for dementia. DHE is considered safe to consume and is present in various dairy products, such as camembert cheese.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Identification of a novel dehydroergosterol enhancing microglial anti-inflammatory activity in a dairy product fermented with Penicillium candidum.
2015

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Dehydroergosterol (DHE) at a concentration of only 2.5 μM and 5 μM suppressed TNF-α production by more than 50%. The proportion of CD11b-positive and CD206-positive M2 type microglia significantly increased after treatment with DHE. Moreover, DHE significantly suppressed the expression of I-A/I-E, CD86 and CD80, but not CD68. In particular, the expression of CD86 and CD80 in CD11b-positive microglia was markedly suppressed compared with CD11b-positive and CD206-positive microglia. DHE also significantly reduced the production of inflammatory cytokines and chemokines (TNF-α, IL-1β, MIP-1α, and IL-12p40/p70), which were highly suppressed in CD11b-positive and CD206-positive M2 type microglia.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:23:19 GMT 2023
Edited
by admin
on Sat Dec 16 09:23:19 GMT 2023
Record UNII
123R6KJQ51
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEHYDROERGOSTEROL
MI  
Common Name English
9(11)-DEHYDROERGOSTEROL
Common Name English
ERGOSTA-5,7,9(11),22-TETRAEN-3-OL, (3.BETA.,22E)-
Systematic Name English
(22E,24R)-ERGOSTA-5,7,9(11),22-TETRAEN-3.BETA.-OL
Systematic Name English
DEHYDROERGOSTEROL, (+)-
Common Name English
(3.BETA.,22E)-ERGOSTA-5,7,9(11),22-TETRAEN-3-OL
Systematic Name English
DEHYDROERGOSTEROL [MI]
Common Name English
Code System Code Type Description
MERCK INDEX
m4147
Created by admin on Sat Dec 16 09:23:19 GMT 2023 , Edited by admin on Sat Dec 16 09:23:19 GMT 2023
PRIMARY Merck Index
CAS
516-85-8
Created by admin on Sat Dec 16 09:23:19 GMT 2023 , Edited by admin on Sat Dec 16 09:23:19 GMT 2023
PRIMARY
PUBCHEM
6436660
Created by admin on Sat Dec 16 09:23:19 GMT 2023 , Edited by admin on Sat Dec 16 09:23:19 GMT 2023
PRIMARY
FDA UNII
123R6KJQ51
Created by admin on Sat Dec 16 09:23:19 GMT 2023 , Edited by admin on Sat Dec 16 09:23:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID601026574
Created by admin on Sat Dec 16 09:23:19 GMT 2023 , Edited by admin on Sat Dec 16 09:23:19 GMT 2023
PRIMARY