Table 3 Studies on the synthesis of HMFS by two-step method

Acidolysis–acidolysis

Tuna oil/PA

Novozym 435

TAGs/FFAs rich in OA

Lipase DF

sn-2 PA, sn-2 DHA content: 52.1%, 15.4%, sn-1,3 OA content: 67%

[44]

Transesterification–transesterification

Hazelnut oil + ethyl palmitate

Novozym 435

TAGs/ARA/DHA-rich single-cell oils

Lipozyme RM IM

PA, ARA, DHA content: 58.9%, 2.7%, 1.5%; sn-2 PA content: 62.5%

[43]

Acidolysis–transesterification

Camellia seed oil + PA

Novozym 435

TAGs/fish oil

Lipozyme TL IM

PA, EPA, DHA, ARA content: 27.88%, 14.50%, 7.38%, 0.99%; sn-2 PA content: 55.97%

[49]

Alcoholysis–transesterification

Tripalmitin + ethanol

Candida sp. 99–125 lipase

2-MAG/ethyl oleate

Candida sp. 99–125 lipase

OPO content: 85.06%; sn-2 PA content: 80.17%

[46]

Alcoholysis–acidolysis

Lard + ethanol

Novozym 435

(Lard + 2-MAG)/(OA + LA)

Lipozyme RM IM

TAG recovery: 66.2 mol%; sn-2 PA content: 66.8%

[45]

Fish oil + ethanol

Novozym 435

2-MAG/OA

Lipozyme RM IM

sn-1,3-OA-sn-2-PUFA-TAG yield: 86.3%

[50]

Lard + ethanol

Novozym 435

(Lard + 2-MAG)/(OA/LA/Ln, 5:2:1, mol)

Lipozyme RM IM

Non-PUFA-containing HMFS yield: 71.3%

Alcoholysis–(acidolysis and transesterification)

Lard + ethanol

Novozym 435

(Lard + 2-MAG)/(OA/LA/Ln, 5:2:1, mol, and PUFA-EEs)

Lipozyme RM IM

sn-1,3-PUFA-HMFS (10% PUFAs at sn-1,3 positions) yield: 69.4%

Esterification–esterification

Glycerol + OA

Novozym 435

Products in step 1/PA

Novozym 435

OPO yield: 15.02%; C52 content: 38.55 wt%; sn-2 PA content: 39.06%

[47]

Esterification–acidolysis

Glycerol + PA

NaOH

Tripalmitin/OA

Lipozyme RM IM

OPO content: 40.23%; 86.62% PA at sn-2 position, 63.74% OA at sn-1,3 positions

[48]

Lipozyme TL IM

OPO content: 32.34%; 92.92% PA at sn-2 position