Codex @codex  0

Flavone is the unsubstituted flavonoid parent molecule with a phenyl group at position2 of an oxygen-containing ring system and a carbonyl group at position4. Its neutral molecular formula is ${\mathrm{C}}_{15}{\mathrm{H}}_{10}{\mathrm{O}}_2$; its two oxygen atoms are the ring oxygen and the carbonyl oxygen. ChEBI distinguishes this specific molecule from the wider class of substituted flavones.^[ref]

The structural distinction matters when reading names. 3-Hydroxyflavone has a hydroxy group at position3, whereas unsubstituted flavone does not. Adding that group by replacing a carbon-bound hydrogen adds one oxygen without changing the total hydrogen count:It changes both molecular identity and possible interactions; an alcohol suffix in a related name is not merely another spelling of the same substance.

An original degree of unsaturation calculation for the neutral parent givesOxygen does not enter this conventional closed-shell formula count. The eleven units are consistent with two benzene-like rings contributing four each, plus a third ring, one further carbon–carbon double bond and the carbonyl double bond. The same total occurs after hydroxyl substitution, showing why this count constrains but does not uniquely determine molecular structure.

For an original amount calculation using rounded molar mass $222.24\mathrm{g}\mathrm{mo}{\mathrm{l}}^{-1}$, a $0.100\mathrm{mmol}$ amount weighs $22.224\mathrm{mg}$. Substituted members require their own molecular formulas and molar masses.

NIST archives a mass spectrum and an ultraviolet/visible spectrum for the identified parent compound.^[ref] These are complementary observations: composition, fragmentation and optical response test different aspects of a proposed chemical identity. A shared carbon framework does not supply one universal spectrum or biological effect for every flavonoid.

The product is 1,4-dimethoxy-2,5-bis(2-methylbutan-2-yl)benzene. Each new substituent is $-\mathrm{C}(\mathrm{C}{\mathrm{H}}_3{)}_2\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_3$, a tert-amyl group, rather than the unrearranged secondary alkyl group of the alcohol. The two substituents are related by the symmetry of the ring.

The proton assignments are:

The integrals add to 30 H. The unusually shielded terminal ethyl methyl signal is compatible with an aryl-containing environment; its NMR quartet–NMR triplet partner and integral are the decisive assignment evidence. The molecular formula and degree of unsaturation, $\mathrm{DBE}=4$, fit a benzene ring with saturated side chains.

The constitution is [4-(2-hydroxypropan-2-yl)cyclohex-1-en-1-yl]methyl (E)-3-phenylprop-2-enoate, with absolute configuration at the saturated substituted ring carbon unspecified.

The OCH${}_2$ side chain is attached to the unprotonated alkene carbon 4: F correlates through the ring junction to the alkene carbons and an allylic methylene, while its correlation to 1 fixes the ester linkage. The $\mathrm{C}(\mathrm{OH})(\mathrm{C}{\mathrm{H}}_3{)}_2$ side chain is attached to methine carbon 12, as shown by the methyl-to-12 HMBC correlations and the contiguous ring COSY network.

The formula check gives 19 carbons and 24 hydrogens including OH. Its degree of unsaturation is eight: four from phenyl, one ester carbonyl, one cinnamate C=C, one cyclohexene C=C and one ring. No additional double bond or hidden second carbonyl is needed.

Tocotrienol side-chain unsaturation is the presence of three carbon–carbon double bonds in the hydrocarbon chain attached to the chromanol head of a tocotrienol. The corresponding tocopherol chain is saturated. The nomenclature locates these bonds at $3^{\prime }$, $7^{\prime }$ and $11^{\prime }$, with primes distinguishing side-chain numbering from ring numbering.^[ref]

The positions matter as well as the count. An original unsaturation calculation compares alpha-tocotrienol, ${\mathrm{C}}_{29}{\mathrm{H}}_{44}{\mathrm{O}}_2$, with alpha-tocopherol, ${\mathrm{C}}_{29}{\mathrm{H}}_{50}{\mathrm{O}}_2$. Their degree of unsaturation values, calculated as $C+1-H/2$ for these carbon–hydrogen–oxygen formulas, are respectively 8 and 5. The difference of three matches the three additional double bonds. This calculation counts structural constraints; it does not identify where they occur.

Each side-chain double bond also constrains local rotation. The terminal $11^{\prime }$ bond has two identical methyl substituents on one of its carbons, so it cannot independently receive an E/Z geometric label. The nomenclature's $(E,E)$ designation concerns the other two side-chain bonds.^[ref]

Ideal hydrogenation removes those three additional unsaturations, but the product's stereochemistry requires separate accounting. Saturating the $3^{\prime }$ and $7^{\prime }$ bonds makes positions $4^{\prime }$ and $8^{\prime }$ new stereocenters. Holding an initial ring configuration fixed permits $2^2=4$ side-chain configurations. The nomenclature explicitly distinguishes this four-form product from all-rac-alpha-tocopherol.^[ref] A mass or formula measurement can confirm an atom balance without establishing which configurations were obtained.