Multiple theories abound. One is that it is from Angloromanilollipobbul(“candy apple”). Another is that it is derived from loll(“to dangle the tongue”) + pop.
1993, Laura S. Frost, “Conjugative Pili and Pilus-Specific Phages”, in D.B. Clewell, editor, Bacterial Conjugation, Springer, →DOI, →ISBN, page 209:
The gene III proteins appear as five lollipops protruding from the end of the phage, and these “balls” can be removed by treatment of the phage with subtilisin, rendering the phage noninfectious.
2010, Renaud Le Goix, Delphine Callen, “Production and Social Sustainability of Private Enclaves in Suburban Landscapes”, in Samer Bagaeen, Ola Uduku, editors, Gated Communities: Social Sustainability in Contemporary and Historical Gated Developments[1], Earthscan, →ISBN, page 107:
The reasons for this containment of gated communities and private streets are not to be sought in morphology (suburban residential developments with lollipops and dead ends are common in France), but rather in local practices by residents.
2019, Joe Baur, Best Hikes Cleveland: The Greatest Views, Wildlife, and Forest Strolls (Best Hikes Near Series), Rowman & Littlefield, →ISBN, page 43:
Mount Pleasant itself is a lollipop trail. Walking along the handle of the lollipop is a breeze—the perfect warm-up for the uphill climb at the beginning of the loop.
