2-Pentanone Production from Hexanoic Acid by Penicillium roqueforti from Blue Cheese: Is This the Pathway Used in Humans?

Table 1

Fragments of 2-pentanone and 2-pentanol derived from ¹H-hexanoic acid, hexanoic-2, 2-D₂ acid, and hexanoic-D₁₁ acid shown in Figure 4.

Peak	(a) 2-Pentanone		(b) 2-Pentanol
	Fragment	𝑚/𝑧	Fragment	𝑚/𝑧
	A: (^1H)-2-pentanone from ^1H-hexanoic acid; CH3CH2CH2COCH3		D: (^1H)-2-pentanol from ^1H-hexanoic acid; CH3CH2CH2CHOHCH3
1	M	86	M − 1	87
2	M–CH3	71	M–CH3	73
3	*(CH3)(CH2)C=OH ⟷ (CH3)(CH2)=C–OH	58		55
4	CH3CO	43	CH3CHOH	45
5	CH3CH2CH2	43	CH3CH2CH2	43
	B: (D)-2-pentanone from hexanoic-2, 2-D2 acid; CH3CH2CH2COCD2H		E: (D)-2-pentanol from hexanoic-2, 2-D2 acid; CH3CH2CH2CHOHCD2H
1	M	88	M − 1	89
2	M–CD2H	71	M–CD2H	73
3	*(CD2H)(CH2)C=OH ⟷ (CD2H)(CH2)=C–OH	60		55
4	CD2HCO	45	CD2HCHOH	47
5	CH3CH2CH2	43	CH3CH2CH2	43
	C: (D)-2-pentanone from hexanoic-D11 acid; CD3CD2CD2COCD2H		F: (D)-2-pentanol from hexanoic acid-D11 acid; CD3CD2CD2CHOHCD2H
1	M	95	M − 1	96
2	M–CD2H	78	M–CD2H	80
3	*(CD2H)(CD2)C=OD ⟷ (CD2H)(CD2)=C–OD	63		61
4	CD2HCO	45	CD2HCHOH	47
5	CD3CD2CD2	50	CD3CD2CD2	50

∗McLafferty rearrangement. **Rearrangement.