10457-66-6

Basic information

• Product Name: Geroquinol
• Synonyms: geroquinol;geranylhydroquinone;GEROQUINOL / 2-TERT-OCTYLHYDROQUINONE;2-[(2E)-3,7-Dimethyl-2,6-octadienyl]hydroquinone;2-[(E)-3,7-Dimethyl-2,6-octadienyl]-1,4-benzenediol;GHQ
• CAS NO: 10457-66-6
• Molecular Formula: C₁₆H₂₂O₂
• Molecular Weight: 246.35
• Mol File: 10457-66-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 61-62°, H. Inouye et al., Ber. 101, 4057 (1968)
• Boiling Point: 413.1 °C at 760 mmHg
• Flash Point: 192.4 °C
• Appearance: /
• Density: 1.035 g/cm³
• Vapor Pressure: 2.06E-07mmHg at 25°C
• Refractive Index: 1.555
• PKA: 10.66±0.18(Predicted)
• CAS DataBase Reference: Geroquinol(CAS DataBase Reference)
• NIST Chemistry Reference: Geroquinol(10457-66-6)
• EPA Substance Registry System: Geroquinol(10457-66-6)

Safety Data

• Hazardous Substances Data: 10457-66-6(Hazardous Substances Data)

Usage

Uses

expertly as a radioprotective agent.

Definition

ChEBI: A polyprenylhydroquinone consisting of hydroquinone in which the hydrogen at position 2 is substituted by a (2E)-3,7-dimethylocta-2,6-dien-1-yl group.

InChI:InChI=1/C16H22O2/c1-12(2)5-4-6-13(3)7-8-14-11-15(17)9-10-16(14)18/h5,7,9-11,17-18H,4,6,8H2,1-3H3/b13-7+

Upstream product

• 106-24-1 Geraniol 
• 123-31-9 hydroquinone 
• 61977-06-8 (E)-3,7-dimethylocta-2,6-dienyl-p-benzoquinone 
• 624-15-7 geraniol 
• 79233-10-6 (E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-4-methoxyphenol 
• 6138-90-5 trans-geranyl bromide 
• 58981-41-2 4-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-phenol 

Downstream Products

• 61977-06-8 (E)-3,7-dimethylocta-2,6-dienyl-p-benzoquinone 
• 137362-28-8 2-((2E,6E)-8-Hydroxy-3,7-dimethyl-octa-2,6-dienyl)-[1,4]benzoquinone 
• 137362-29-9 2-((E)-4-Hydroxy-3,7-dimethyl-octa-2,6-dienyl)-[1,4]benzoquinone 
• 50801-25-7 (2E,6E)-8-(3,6-Dioxo-cyclohexa-1,4-dienyl)-2,6-dimethyl-octa-2,6-dienal 
• 63025-46-7 8-(2',5'-dihydroxyphenyl)-2,6-dimethyl-2,6-octadien-1-ol 
• 123164-53-4 cordiachromene 
• 714956-90-8 1,4-Bis-benzyloxy-2-((E)-3,7-dimethyl-octa-2,6-dienyl)-benzene 
• 23176-80-9 (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,4-phenylene diacetate 
• 714956-89-5 1,4-Bis-benzyloxy-2-[(2E,6E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienyl]-benzene 
• 714956-91-9 (2E,6E)-8-(2,5-Bis-benzyloxy-phenyl)-2,6-dimethyl-octa-2,6-dien-1-ol 
• 714956-92-0 1,4-Bis-benzyloxy-2-((2E,6E)-8-chloro-3,7-dimethyl-octa-2,6-dienyl)-benzene 
• 50906-59-7 alliodorine EE 

Relevant articles and documents

Potential role of two cytochrome P450s obtained from Lithospermum erythrorhizon in catalyzing the oxidation of geranylhydroquinone during Shikonin biosynthesis

Shikonin is a natural naphthoquinone derivative that specifically occurs in boraginaceous plants, and the major active ingredient of the medicinal plant Lithospermum erythrorhizon. Previously, a cytochrome P450 oxygenase (CYP) CYP76B74 catalyzing 3″-hydroxylation of geranylhydroquinone (GHQ) — a key intermediate of shikonin biosynthesis, was identified from cultured cells of Arnebia euchroma. However, the enzymes catalyzing oxidation of the geranyl side-chain of GHQ from L. erythrorhizon remain unknown. In this study, we performed transcriptome analysis of different tissues (red roots and green leaves/stems) from L. erythrorhizon using RNA sequencing technology. Highly expressed CYP genes found in the roots were then heterologously expressed in Saccharomyces cerevisiae and functionally screened with GHQ as the substrate. As the result, two CYPs of CYP76B subfamily catalyzing the oxidation of GHQ were characterized. CYP76B100 catalyzed the hydroxylation of the geranyl side-chain of GHQ at the C-3″ position to form 3″-hydroxyl geranylhydroquinone (GHQ-3″-OH). The enzyme CYP76B101 carried out oxidation reaction of GHQ at the C-3″ position to produce a 3″-carboxylic acid derivative of GHQ (GHQ-3″-COOH) as well as GHQ-3″-OH. This enzyme-catalyzed oxidation reaction with GHQ as the substrate is reported for the first time. This study implicates CYP76B100 and CYP76B101 as having a potential role in shikonin biosynthesis in L. erythrorhizon.

Construction of a meroterpenoid-like compound collection by precursor-assisted biosynthesis

Natural products (NPs) and their derivatives play a pivotal role in drug discovery due to their complexity and diversity. The strategies to rapidly generate NP-like compounds offer unique opportunities to access bioactive compounds. Here we present a new approach, precursor-assisted biosynthesis (PAB), for the creation of NP-like compounds by combination of artificial supplementation of common precursors and divergent post-modifications of precursor-deficient fungi. This method was applied to construct a meroterpenoid-like compound collection containing 43 compounds with diverse molecular scaffolds. Extensive bioactive screening of the collection revealed novel STING (stimulator of interferon genes) inhibitors, cytotoxic and antifungal compounds. This result indicates that PAB is an effective methodology for producing compound collections for the purpose of drug discovery.