Eye of the Wrinkler (99,999,999) *no true effect on gameplay, but can be useful
777,777

14th - 500M - Total HC: 850,188,126
Sugar Baking (200M)
Diabetica Daemonicus (300M)

15th - 1B - Total HC: 1,850,188,126
Sugar Craving (400M)
Sugar Aging Process (600M)

16th - 2B - Total HC: 3,850,188,126
Sucralosia Inutilis (1B)
Sugar Crystal Cookie (1B)

17th - 2,111,111,110 - Total HC: 5,961,299,236
Shimmering Veil (999,999,999)
Keepsakes (1,111,111,111)

18th - 8B for ascension 19 - Total HC: 13,961,299,236
19th - 29,999,999,970 (-8B from previous ascension) = 21,999,999,970 - Total HC: 35,961,299,206
Cosmic Beginner's Luck (14,999,999,985)
Reinforced Membrane (14,999,999,985)

20nd - 83B for ascension 21 - Total HC: 118,961,299,206
21st - 333B (-83B from previous ascensions) = 250B - Total HC: 368,961,299,206
Box of Pastries (333B)

22nd - 333B - Total HC: 701,961,299,206
Maybe Cookies (333B)

23rd - 333B - Total HC: 1,034,961,299,206
Not Cookies (333B)

Permaslots
==========
(440 - 36B HC [when you unlock Cosmic Beginner's Luck]) - slot these upgrades in as you unlock the slots
Permaslot 1 - highest illion fingers upgrade
Permaslot 2 - highest kitten
Permaslot 3 - highest Fractal engine upgrade
Permaslot 4 - 2nd highest kitten
Permaslot 5 - omelette

(36B - when you unlock the 450 of every building Biscuit)
Permaslots 1 and 2 (pick TWO) - highest illion fingers upgrade, highest building biscuit, 3rd highest kitten, omelette
Permaslot 3 - highest kitten
Permaslot 4 - highest Fractal engine upgrade
Permaslot 5 - 2nd highest kitten

(After you unlock the 450 of every building Biscuit)
Permaslot 1 - highest illion fingers upgrade OR second highest building biscuit OR omelette
Permaslot 2 - highest kitten
Permaslot 3 - highest Fractal engine upgrade
Permaslot 4 - 2nd highest kitten
Permaslot 5 - highest building biscuit