78804-17-8

Basic information

• Product Name: (-)-ZEYLENOL
• Synonyms: (1S,2R,3S,4R)-2-[(Benzoyloxy)methyl]-5-cyclohexene-1,2,3,4-tetrol 4-benzoate;((1R,2S,5R,6S)-5-(Benzoyloxy)-1,2,6-trihydroxycyclo-hex-3-en-1-yl)methyl benzoate
• CAS NO: 78804-17-8
• Molecular Formula: C₂₁H₂₀O₇
• Molecular Weight: 384.382
• Product Categories: Miscellaneous Natural Products
• Mol File: 78804-17-8.mol

Chemical Properties

• Melting Point: 131-132℃
• Boiling Point: 549.615oC at 760 mmHg
• Flash Point: 192.395oC
• Appearance: /
• Density: 1.41
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (-)-ZEYLENOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ZEYLENOL(78804-17-8)
• EPA Substance Registry System: (-)-ZEYLENOL(78804-17-8)

Safety Data

• Hazardous Substances Data: 78804-17-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
(-)-ZEYLENOL is used as a pharmaceutical agent for its anti-inflammatory and anti-tumor properties. It is particularly valuable in scientific research experiments aimed at developing new treatments for inflammation and cancer.
Used in Drug Delivery Systems:
In the pharmaceutical industry, (-)-ZEYLENOL can be utilized as a component in drug delivery systems to enhance the efficacy and targeted delivery of anti-inflammatory and anti-tumor medications. This application can improve the bioavailability and therapeutic outcomes of such drugs.
Used in Nutraceuticals and Dietary Supplements:
Given its health-promoting properties, (-)-ZEYLENOL can be incorporated into nutraceuticals and dietary supplements to support anti-inflammatory and anti-tumor benefits for consumers seeking natural health solutions.
Used in Cosmetics and Personal Care:
Due to its anti-inflammatory properties, (-)-ZEYLENOL may also find use in the cosmetics and personal care industry, where it can be formulated into products designed to soothe and protect the skin, as well as promote overall skin health.

InChI:InChI=1/C21H20O7/c22-17-12-11-16(20(25)28-15-9-5-2-6-10-15)18(23)21(17,26)13-27-19(24)14-7-3-1-4-8-14/h1-12,16-18,22-23,26H,13H2/t16-,17+,18+,21-/m1/s1

Upstream product

• 172877-75-7 (3aS,7aR)-methyl 2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylate 
• 172877-74-6 (-)-(3aS,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxole-3a-carboxylic acid 
• 172877-76-8 ((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methanol 
• 32359-20-9 (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid 
• 1379659-90-1 C₃₀H₃₈O₇Si 
• 1379659-88-7 C₁₆H₃₀O₅Si 
• 1379659-87-6 C₁₆H₂₈O₅Si 
• 1379659-86-5 tert-butyl(((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methoxy)dimethylsilane 
• 869353-28-6 1-O-acetyl-2,3-O-isopropylidene-D-mannofuranose 
• 253589-92-3 C₃₅H₅₀O₇Si₃ 
• 253589-90-1 C₂₆H₂₅BrO₇ 
• 253589-91-2 C₂₆H₂₆O₇ 
• 253589-89-8 C₂₆H₂₃BrO₅ 
• 253589-82-1 C₁₉H₃₁BrO₅Si 

Downstream Products

• 193410-84-3 (-)-Tonkinenin A 
• 29399-87-9 (+)-Pipoxide 
• 78804-18-9 (+)-(1R,2S,3R,4S)-2-benzoyloxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,3-diacetate 4-benzoate 
• 113467-89-3 (+)-(1R,2S,3R,4S)-2-benzoyloxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,2,3-triacetate 4-benzoate 
• 113467-91-7 (+)-(1R,2R,3S,4R,5S,6R)-3-benzoyloxymethyl-7-oxabicyclo<4.1.0>heptane-2,3,4,5-tetrol 5-benzoate 
• 113467-90-6 (-)-(1R,2S,3R,4S)-2-benzoyloxymethyl-1,2-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetrol 4-benzoate 
• 207971-83-3 (-)-Uvarigranol G 
• 358748-29-5 2-O-acetylzeylenone 
• 164204-79-9 1-epizeylenol 6-acetate 
• 78804-18-9 Zeylenyl Diacetate 

Relevant articles and documents

Stereoselective total synthesis of (?)-zeylenol, a key intermediate for the synthesis of (+)-pipoxide, (?)-uvarigranol G and (?)-tonkinenin A

Total synthesis of (?)-zeylenol, a key intermediate for the synthesis of (+)-pipoxide, (?)-uvarigranol G and (?)-tonkinenin A was achieved from commercially available starting material D-mannose. The key steps are mixed aldol condensation, Grignard reaction, ring closing metathesis and regioselective benzoylation.

Photooxygenation of a microbial arene oxidation product and regioselective Kornblum-DeLamare rearrangement: Total synthesis of zeylenols and zeylenones

We report the enantioselective total syntheses of zeylenol (+)-1, as well as its congeners (-)-7 and 16, and of 3-O-debenzoylzeylenone 28. To this end, a new variant of the Kornblum-DeLaMare rearrangement, which utilises neighbouring-group participation to impart regioselectivity, has been developed. The approach employs photooxygenation of building blocks derived from a microbial arene oxidation product. New light on a Korny rearrangement: Biooxidation of benzoic acid with R. eutrophus B9 gives a dearomatised diene diol acid that allows concise access to the zeylenol and zeylenone family of polyoxygenated cyclohexene natural products. The synthesis employs diene photooxygenation and a new regioselective variant of the Kornblum-DeLaMare endoperoxide fragmentation has been developed (see scheme).

The first enantiocontrolled synthesis of naturally occurring polyoxygenated cyclohexenylmethanol dibenzoates (-)-zeylenol, (-)-uvarigranol G, (-)-tonkinenin A and (+)-pipoxide

The first enanticontrolled synthesis of five naturally occurring polyoxygenated cyclohexenylmethanol dibenzoates has been achieved to confirm three [(-)-zeylenol, (-)-uvarigranol G, (+)-pipoxide], revise one [(-)-tonkinenin A] and disprove one [(-)-epizey

CYCLOHEXANE OXIDE DERIVATIVES FROM KAEMPFERIA ANGUSTIFOLIA AND KAEMPFERIA SPECIES

(-)-(3S,4R,5S,7S)-5-Benzoyloxymethyl-6-oxadicyclo-hept-1-ene-3,4-diol 3-benzoate and the two (+)-zeylenol related substances, (-)-(1R,2S,3R,4S)-2-benzoyloxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,4-dibenzoate, and (1R,2S,3R,4S)-2-hydroxymethylcyclohex-5-ene-1,2,3,4-tetrol 1,4-dibenzoate, together with 2'-hydroxy-4,4',6'-trimethoxychalcone, were isolated from the rhizomes of Kaempferia angustifolia, in addition to crotepoxide, boesenboxide and (+)-zeylenol.The rhizomes of an unnamed Kaempferia species have also been found to contain the zeylenol derivatives. - Keywords: Kaempferia angustifolia; Kaempferia sp.; Zingiberaceae; (-)-pipoxide; oxygenated cyclohexane; (+)-zeylenol.

STUDIES ON HIGHLY OXIDIZED CYCLOHEXANES.STRUCTURE AND ABSOLUTE CONFIGURATION ASSIGNMENTS.

The absolute configurations of pipoxide, ferrudiol and zeylenol, pictured below, are found to parallel those of crotepoxide and senepoxide, suggesting a unified biogenesis.