13601-88-2

Basic information

• Product Name: 1-Phenanthrenecarboxaldehyd
• Synonyms: 1-Phenanthrenecarboxaldehyd;(1R)-1,2,3,4,4a,9,10,10aα-Octahydro-1,4aβ-dimethyl-7-(1-methylethyl)phenanthrene-1α-carbaldehyde;13-Isopropylpodocarpa-8,11,13-trien-18-al;Abieta-8,11,13-trien-18-al;Dehydroabietal;Dehydroabietinal;dehydroabietadienal
• CAS NO: 13601-88-2
• Molecular Formula: C₂₀H₂₈O
• Molecular Weight: 284.44
• Mol File: 13601-88-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 53-55 °C
• Boiling Point: 190-194 °C(Press: 2-3 Torr)
• Appearance: /
• Density: 1.022±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1-Phenanthrenecarboxaldehyd(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenanthrenecarboxaldehyd(13601-88-2)
• EPA Substance Registry System: 1-Phenanthrenecarboxaldehyd(13601-88-2)

Safety Data

• Hazardous Substances Data: 13601-88-2(Hazardous Substances Data)

Usage

Physical state

Pale yellow solid at room temperature

Aromaticity

Highly aromatic compound with a strong odor

Uses

Raw material in the production of dyes, pigments, and pharmaceuticals; reagent in organic synthesis, especially in the preparation of various aromatic compounds

Toxicity

Moderately toxic, can irritate skin, eyes, and respiratory system

Handling precautions

Should be handled with caution

Presence in consumer products

Not widely used, may be found in industrial and laboratory settings.

InChI:InChI=1S/C20H28O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12-14,18H,5,7,9-11H2,1-4H3/t18?,19-,20?/m1/s1

Upstream product

• 31148-95-5 (+)-dehydroabietylnitrile 
• 1446-61-3 leelamine 
• 1228-43-9 Dehydroabietol 
• 850380-03-9 Dehydroabietylamine 
• 911316-54-6 dehydroabietic acid 
• 3513-69-7 methyl ester of levopimaric acid 
• 79-54-9 levopimaric acid 
• 1235-74-1 Methyl dehydroabietate 
• 1740-19-8 dehydroabietic acid 
• 864060-42-4 abieta-8,11,13-trien-18-(N-methoxy-N-methyl)amide 
• 97640-46-5 levopimaradien-18-ol 
• 666-84-2 abietinol 
• 22478-66-6 dehydroabietic acid chloride 
• 3772-55-2 dehydroabietinol 

Downstream Products

• 79328-77-1 (1R,4aS)-1-[(E)-2-(4-Chloro-benzenesulfonyl)-vinyl]-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene 
• 514-62-5 ferruginol 
• 22478-65-5 18-norabieta-8,11,13-trien-4-ol 
• 105037-83-0 7-keto-15-hydroxydehydroabietane 
• 67119-95-3 (5S,10S)-abieta-9,11,13-trien-14-ol 
• 3772-55-2 dehydroabietinol 
• 33980-70-0 4-hydroxy-19-nor-dehydroabietane 

Relevant articles and documents

Bispericyclic Diels–Alder Dimerization of ortho-Quinols in Natural Product (Bio)Synthesis: Bioinspired Chemical 6-Step Synthesis of (+)-Maytenone

Many natural products of plant or microbial origins are derived from enzymatic dearomative oxygenation of 2-alkylphenolic precursors into 6-alkyl-6-hydroxycyclohexa-2,4-dienones. These so-called ortho-quinols cyclodimerize via a remarkably selective bispericyclic Diels–Alder reaction. Whether or not the intervention of catalytic or dirigent proteins is involved during this final step of the biosynthesis of these natural products, this cyclodimerization of ortho-quinols can be chemically reproduced in the laboratory with the same strict level of site-specific regioselectivity and stereoselectivity. This unique yet unified process, which finds its rationale in the inherent chemical reactivity of those ortho-quinols, is illustrated herein by an efficient and bioinspired first chemical synthesis of one of the most structurally complex and synthetically challenging examples of such natural cyclodimers, the bisditerpenoid (+)-maytenone.

NEW DERIVATES OF DHAA WITH ELECTROSTATIC TUNING

Dehydroabietic acid derivatives according to Formula Ia or Formula Ib and all stereoisomers thereof, having a linker chain A of 1 to 10 atoms selected from carbon, nitrogen and oxygen to a group X capable of being negatively charged at a physiological pH and covalently attached to the linker chain A, selected from carboxyl, sulfate, sulfonate and phosphate groups. The Dehydroabietic acid derivatives are useful for therapeutic treatment of hyperexcitablity diseases

Synthesis and biological evaluation of dehydroabietic acid derivatives

A series of C18-oxygenated derivatives of dehydroabietic acid were synthesized from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities.