Grindelic Acid
Basic information
- CAS
1438-57-9- Standard SMILES
CC1=CC[C@H]2C(C)(C)CCC[C@]2(C)[C@@]12CC[C@@](C)(CC(=O)O)O2- InChIKey
XLWWERNKTLITEF-MVJPYGJCSA-N- Molecular formula
- C20H32O3
- Average molar mass
- 320.5 g/mol
- Monoisotopic mass
- 320.23514488
Overview
grindelic acid has been reported in Grindelia hirsutula, Grindelia boliviana, and other organisms with data available.
Names & identifiers
- Preferred name
- Grindelic Acid
- IUPAC
- 2-[(2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
- English name
- (2R,5S)-4,4'aα,5,5',6',7',8',8'a-Octahydro-2',5,5',5',8'aβ-pentamethylspiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid
- Molecular formula
- C20H32O3
- Molecular weight
- 320.47
Names & synonyms
Grindelic acid1438-57-94QX9FCD1INLabd-7-en-15-oic acid, 9,13-epoxy-2-[(2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid2-((2'S,4aS,8R,8aS)-2',4,4,7,8a-pentamethylspiro(2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane)-2'-yl)acetic acidRefChem:144438DTXCID101016580DTXSID10878535(-)-GRINDELIC ACIDUNII-4QX9FCD1INGRINDELIC ACID [MI]
Show more names
9,13-epoxylabd-7-en-15-oic acidGrindelic acid >=95% (LC/MS-ELSD)(5β,9S,10α,13R)-9,13-Epoxylabd-7-en-15-oic acid(2R,5S)-4,4'aα,5,5',6',7',8',8'a-Octahydro-2',5,5',5',8'aβ-pentamethylspiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid(2S,5R)-4,4'aβ,5,5',6',7',8',8'a-Octahydro-2',5,5',5',8'aα-pentamethylspiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acidSpiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid, 4,4'a,5,5',6',7',8',8'a-octahydro-2',5,5',5',8'a-pentamethyl-, (1'R,4'aS,5S,8'aS)-
CHEMBL2419211SCHEMBL37300568(2R,5S)-4,4'aalpha,5,5',6',7',8',8'a-Octahydro-2',5,5',5',8'abeta-pentamethylspiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acidSPIRO(FURAN-2(3H),1'(4'H)-NAPHTHALENE)-5-ACETIC ACID, 4,4'A,5,5',6',7',8',8'A-OCTAHYDRO-2',5,5',5',8'A-PENTAMETHYL-, (1'R-(1'.ALPHA.(S*),4'A.ALPHA.,8'A.BETA.))-Grindelic acid, >=95% (LC/MS-ELSD)Q27260380SPIRO(FURAN-2(3H),1'(4'H)-NAPHTHALENE)-5-ACETIC ACID, 4,4'A,5,5',6',7',8',8'A-OCTAHYDRO-2',5,5',5',8'A-PENTAMETHYL-, (1'R,4'AS,5S,8'AS)-
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 549
Physicochemical properties
- Melting point
- 100 · 100-101°
- alpha
- -102.2 ° · D -102.2°
- Boiling point
- 434.7 · 434.7±28.0 °C(Predicted)
- Density
- 1.07 · 1.07±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- form
- solid
- pka
- 4.34 · 4.34±0.10(Predicted)
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChI
- 1S/C20H32O3/c1-14-7-8-15-17(2,3)9-6-10-19(15,5)20(14)12-11-18(4,23-20)13-16(21)22/h7,15H,6,8-13H2,1-5H3,(H,21,22)/t15-,18-,19-,20+/m0/s1
- InChIKey
- XLWWERNKTLITEF-MVJPYGJCSA-N
- SMILES
- CC1=CC[C@H]2C(C)(C)CCC[C@]2(C)[C@@]13CC[C@@](C)(CC(O)=O)O3
- LogP
- 5.65 · 5.650 (est)
- FDA UNII
- 4 QX9FCD1IN · 4QX9FCD1IN
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 25 · NA.25
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
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
Uses(-)-Grindelic Acid is a natural diterpene with potential pharmaceutical applications including Nox4 inhibition and antitumor activity.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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