80557-12-6

Basic information

• Product Name: Grifolic acid
• Synonyms: Grifolic acid
• CAS NO: 80557-12-6
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.49778
• Product Categories: Herb extract
• Mol File: 80557-12-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 93-94 °C(Solv: hexane (110-54-3))
• Boiling Point: 557.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.086±0.06 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.22±0.25(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: Grifolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Grifolic acid(80557-12-6)
• EPA Substance Registry System: Grifolic acid(80557-12-6)

Safety Data

• Hazardous Substances Data: 80557-12-6(Hazardous Substances Data)

Usage

Uses

Grifolic Acid is a selective partial GPR120 agonist. Grifolic Acid induces ERK and [Ca2+]i responses in cells expressing GPR120, but has no effects on those expressing GPR40.

Synthetic route

7-hydroxy-2,2,5-trimethyl-8-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)-4H-benzo[d][1,3]dioxin-4-one → Grifolic acid (80557-12-6)

Conditions	Yield
With potassium tert-butylate; water In diethyl ether at 25℃; for 72h;	89%

Grifolic acid (80557-12-6) → 2,7-dimethyl-5-hydroxy-2-[(3E)-4,8-dimethyl-3,7-nonadienyl]-2H-1-benzopyran-6-carboxylic acid (635703-89-8)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 90℃; for 0.5h;	73%

CYANAMID (420-04-2) + Grifolic acid (80557-12-6) → 2-Hydroxy-4-methoxy-6-methyl-3-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl)-benzoic acid methyl ester

Conditions	Yield
In diethyl ether	5 mg

Grifolic acid (80557-12-6) → grifolin (6903-07-7)

Conditions	Yield
With methanol; sodium hydroxide at 60℃; for 3h;

Grifolic acid (80557-12-6) → (-)-daurichromenic acid + (+)-daurichromenic acid (82003-90-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 90℃; for 0.5h;	A 203 mg B 208 mg

Grifolic acid (80557-12-6) + methyl iodide (74-88-4) → trimethylgrifolinol

Conditions	Yield
With potassium carbonate In acetone for 10h; Heating;	3.4 mg

Grifolic acid (80557-12-6) → 2-[3-((E)-4,8-Dimethyl-nona-3,7-dienyl)-3-methyl-oxiranylmethyl]-5-methyl-benzene-1,3-diol

Conditions	Yield
Multi-step reaction with 2 steps 1: 1percent NaOH-MeOH / 3 h / 60 °C 2: 219 mg / m-chloroperbenzoic acid / CHCl3 / 3 h / -30 °C View Scheme

Grifolic acid (80557-12-6) → (R)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-5-methoxy-2,7-dimethyl-chroman-3-one

Conditions	Yield
Multi-step reaction with 5 steps 1: 1percent NaOH-MeOH / 3 h / 60 °C 2: 219 mg / m-chloroperbenzoic acid / CHCl3 / 3 h / -30 °C 3: 131 mg / p-toluenesulfonic acid monohydrate / dioxane / 3 h / Ambient temperature 4: 8 mg / diethyl ether 5: 7 mg / Jones' reagent / acetone / 2 h View Scheme
Multi-step reaction with 5 steps 1: 1percent NaOH-MeOH / 3 h / 60 °C 2: 219 mg / m-chloroperbenzoic acid / CHCl3 / 3 h / -30 °C 3: 25 mg / p-toluenesulfonic acid monohydrate / dioxane / 3 h / Ambient temperature 4: 8 mg / diethyl ether 5: 5 mg / Jones' reagent / acetone / 2 h View Scheme

Grifolic acid (80557-12-6) → (2R,3R)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2,7-dimethyl-chroman-3,5-diol

Conditions	Yield
Multi-step reaction with 3 steps 1: 1percent NaOH-MeOH / 3 h / 60 °C 2: 219 mg / m-chloroperbenzoic acid / CHCl3 / 3 h / -30 °C 3: 131 mg / p-toluenesulfonic acid monohydrate / dioxane / 3 h / Ambient temperature View Scheme

Grifolic acid (80557-12-6) → (2R,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2,7-dimethyl-chroman-3,5-diol

Conditions	Yield
Multi-step reaction with 3 steps 1: 1percent NaOH-MeOH / 3 h / 60 °C 2: 219 mg / m-chloroperbenzoic acid / CHCl3 / 3 h / -30 °C 3: 25 mg / p-toluenesulfonic acid monohydrate / dioxane / 3 h / Ambient temperature View Scheme

Grifolic acid (80557-12-6) → (2R,3R)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-5-methoxy-2,7-dimethyl-chroman-3-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 1percent NaOH-MeOH / 3 h / 60 °C 2: 219 mg / m-chloroperbenzoic acid / CHCl3 / 3 h / -30 °C 3: 131 mg / p-toluenesulfonic acid monohydrate / dioxane / 3 h / Ambient temperature 4: 8 mg / diethyl ether View Scheme

Grifolic acid (80557-12-6) → (2R,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-5-methoxy-2,7-dimethyl-chroman-3-ol

Conditions	Yield
Multi-step reaction with 4 steps 1: 1percent NaOH-MeOH / 3 h / 60 °C 2: 219 mg / m-chloroperbenzoic acid / CHCl3 / 3 h / -30 °C 3: 25 mg / p-toluenesulfonic acid monohydrate / dioxane / 3 h / Ambient temperature 4: 8 mg / diethyl ether View Scheme

Downstream Products

• 6903-07-7 grifolin 
• 82003-90-5 (+)-daurichromenic acid 

Relevant articles and documents

Meroterpenoid total synthesis: Conversion of geraniol and farnesol into amorphastilbol, grifolin and grifolic acid by dioxinone-β-keto-acylation, palladium catalyzed decarboxylative allylic rearrangement and aromatization

Biomimetic total syntheses of resorcinols amorphastilbol, grifolin and grifolic acid have been completed in four steps starting from geraniol and farnesol without the use of phenolic protection. The key steps involve C-acylation of dioxinone-β-keto esters, followed by palladium catalyzed decarboxylative allylic rearrangement and biomimetic aromatization.