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(3S,3aR,5aS,8aS,8bS)-5a,7,8,8a-Tetrahydro-3-hydroxy-7,7-dimethyl-1-oxo-3H,6H-3a,8b-methano-1H-indeno(4,5-c)furan-4-carboxaldehyde

HCID 24839986
NotesReactions
Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
2212-99-9
Standard SMILES
CC1(C)C[C@H]2C=C(C=O)[C@]34C[C@]3(C(=O)O[C@@H]4O)[C@H]2C1
InChIKey
BIUVCPLWWOLECJ-WMABBAGQSA-N
Molecular formula
C15H18O4
Average molar mass
262.3 g/mol
Monoisotopic mass
262.12050905

Overview

Marasmic acid has been reported in Hygrophorus with data available.

Names & identifiers

Preferred name
(3S,3aR,5aS,8aS,8bS)-5a,7,8,8a-Tetrahydro-3-hydroxy-7,7-dimethyl-1-oxo-3H,6H-3a,8b-methano-1H-indeno(4,5-c)furan-4-carboxaldehyde
IUPAC
(1S,2S,6S,9R,10S)-10-hydroxy-4,4-dimethyl-12-oxo-11-oxatetracyclo[7.3.1.01,9.02,6]tridec-7-ene-8-carbaldehyde
English name
marasmic acid
Molecular formula
C15H18O4
Molecular weight
262.3

Names & synonyms

Marasmic acid2212-99-9S74EQ59M5CNSC-318506(3S,3AR,5AS,8AS,8BS)-5A,7,8,8A-TETRAHYDRO-3-HYDROXY-7,7-DIMETHYL-1-OXO-3H,6H-3A,8B-METHANO-1H-INDENO(4,5-C)FURAN-4-CARBOXALDEHYDERefChem:906059(1S,2S,6S,9R)-10-hydroxy-4,4-dimethyl-12-oxo-11-oxatetracyclo(7.3.1.01,9.02,6)tridec-7-ene-8-carbaldehydeLACHNELLA FUNGUS(1S,2S,6S,9R,10S)-10-hydroxy-4,4-dimethyl-12-oxo-11-oxatetracyclo[7.3.1.01,9.02,6]tridec-7-ene-8-carbaldehydeCCRIS 17013H,6H-3A,8B-METHANO-1H-INDENO(4,5-C)FURAN-4-CARBOXALDEHYDE, 5A,7,8,8A-TETRAHYDRO-3-HYDROXY-7,7-DIMETHYL-1-OXO-, (3S-(3.ALPHA.,3A.BETA.,5A.BETA.,8A.BETA.,8B.BETA.))-3H,6H-3a,8b-Methano-1H-indeno[4,5-c]furan-4-carboxaldehyde, 5a,7,8,8a-tetrahydro-3-hydroxy-7,7-dimethyl-1-oxo-, [3S-(3.alpha.,3a.beta.,5a.beta.,8a.beta.,8b.beta.)]-
Show more names
NSC3185063H,6H-3a,8b-Methano-1H-indeno[4,5-c]furan-4-carboxaldehyde, 5a,7,8,8a-tetrahydro-3-hydroxy-7,7-dimethyl-1-oxo-, (3S,3aR,5aS,8aS,8bS)-
NSC 318506UNII-S74EQ59M5Corb1701957AKOS040747136HY-126637T257773H,6H-3A,8B-METHANO-1H-INDENO(4,5-C)FURAN-4-CARBOXALDEHYDE, 5A,7,8,8A-TETRAHYDRO-3-HYDROXY-7,7-DIMETHYL-1-OXO-, (3S,3AR,5AS,8AS,8BS)-

Database identifiers

CAS
2212-99-9
PubChem CID
24839986
UNII
S74EQ59M5C
Nikkaji
J470.640D

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
63.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
19
Formal charge
0
Complexity
534

Physicochemical properties

Melting point
173.5 °C · 173.5°C
Boiling point
339.23 °C · 339.23°C (rough estimate)
Density
1.0721 · 1.0721 (rough estimate)
refractive index
1.435 · 1.4350 (estimate)
pka
11.22 · 11.22±0.60(Predicted)
EWG's Food Scores
1 · 1
FDA UNII
74 EQ59M5C · S74EQ59M5C

Chemistry & industry

Applications · 1 item

UsesMarasmic acid is a sesquiterpenoid with unsaturated dialdehyde functionality, first isolated from the Basidiomycete Marasmus conigenus. Marasmic acid has antibacterial, antifungal, cytotoxic and mutagenic activities, and its broad-spectrum activity is related to the α,β-unsaturated aldehyde group. However, its detailed biological mechanism of action has not been clarified. Previous studies have suggested that marasmic acid may exert its effects by reacting with endogenous nucleophiles or forming pyrrole derivatives. This study found that marasmic acid interferes with the membrane sensor histidine kinase MoSln1p of M. oryzae, superactivates the HOG pathway and causes cell death, indicating that its mechanism of action is different from other unsaturated dialdehyde sesquiterpenoids.

Suppliers4 total

上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]

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Compound notes

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