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[9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate

HCID 3482908
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Basic information

CAS
65725-11-3
Standard SMILES
C=C1C(=O)OC2C3C(CO)=CC(=O)C3=C(C)CC(OC(=O)Cc3ccc(O)cc3)C12
InChIKey
UMVSOHBRAQTGQI-UHFFFAOYSA-N
Molecular formula
C23H22O7
Average molar mass
410.4 g/mol
Monoisotopic mass
410.13655304

Overview

[9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate has been reported in Cichorium endivia, Cichorium intybus, and Cichorium pumilum with data available.

Names & identifiers

Preferred name
[9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate
IUPAC
[9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate
English name
Lactucopicrin
Molecular formula
C23H22O7
Molecular weight
410.42

Names & synonyms

Lactupicrin(3aR,4S,9aS,9bR)-9-(Hydroxymethyl)-6-methyl-3-methylene-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate[(3aR,4S,9aS,9bR)-9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetateBenzeneacetic acid, 4-hydroxy-, (3aR,4S,9aS,9bR)-2,3,3a,4,5,7,9a,9b-octahydro-9-(hydroxymethyl)-6-methyl-3-methylene-2,7-dioxoazuleno[4,5-b]furan-4-yl ester

Database identifiers

CAS
65725-11-3
PubChem CID
3482908

Properties

Computed structural properties

XLogP
1.1
Topological polar surface area
110 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
7
Rotatable bonds
5
Heavy atoms
30
Formal charge
0
Complexity
844

Experimental & physicochemical properties

Melting Point132 - 178 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
146 °C · 146 °C
Boiling point
686 · 686.0±55.0 °C(Predicted)
Density
1.4 · 1.40±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
form
Solid
pka
9.79 · 9.79±0.15(Predicted)
color
White to off-white
InChIKey
UMVSOHBRAQTGQI-XGARDCMYSA-N
SMILES
C1(CC(O[C@@H]2[C@@]3([H])C(=C)C(=O)O[C@]3([H])[C@]3([H])C(C(=O)C=C3CO)=C(C)C2)=O)=CC=C(O)C=C1
LogP
2.24 · 2.240 (est)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
317 · H317
Precautionary statements
280 · P280-P302+P352
WGK Germany
3 · WGK 3
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
1 · Skin Sens. 1

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 3
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H317
Hazard Classifications
Skin Sens. 1
Precautionary statements
P280-P302+P352

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm
Applications · 1 item

UsesLactupicrin (Lactucopicrin) exhibits analgesic, sedative, antimalarial activities and atheroprotective effect. Lactupicrin inhibits acetylcholinesterase (AChE) with an IC50 of 150.3 μM. Lactupicrin is an orally active characteristic bitter sesquiterpene lactone[1][2][3][4][5].

Additional notes · 1 item

DefinitionChEBI: Lactucopicrin is an azulenofuran, a cyclic terpene ketone, an enone, a member of phenols, a sesquiterpene lactone and a primary alcohol. It has a role as a plant metabolite, a sedative and an antimalarial. It is functionally related to a 4-hydroxyphenylacetic acid and a lactucin.

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